SE434945B - Karbostyrilderivat - Google Patents

Karbostyrilderivat

Info

Publication number: SE434945B
Authority: SE; Sweden
Prior art keywords: carbon atoms; crystals; dihydrocarbostyril; propoxy; group
Prior art date: 1978-03-30

Application number

SE7902794A

Other languages

English (en)

Swedish (sv)

Other versions

SE7902794L (sv

Inventor

K Banno

T Fujioka

Y Oshiro

K Nakagawa

Original Assignee

Otsuka Pharma Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-03-30

Filing date

1979-03-29

Publication date

1984-08-27

1979-03-29 Application filed by Otsuka Pharma Co Ltd filed Critical Otsuka Pharma Co Ltd

1979-10-01 Publication of SE7902794L publication Critical patent/SE7902794L/xx

1984-08-27 Publication of SE434945B publication Critical patent/SE434945B/sv

Links

LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 47
-1 3,4,5-trimethoxybenzoyloxy Chemical group 0.000 claims description 144
125000004432 carbon atom Chemical group C* 0.000 claims description 66
239000003795 chemical substances by application Substances 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
239000000739 antihistaminic agent Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 15
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 15
230000000694 effects Effects 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
230000001105 regulatory effect Effects 0.000 claims description 14
210000003169 central nervous system Anatomy 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000004423 acyloxy group Chemical group 0.000 claims description 11
230000001387 anti-histamine Effects 0.000 claims description 11
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
238000006467 substitution reaction Methods 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
229940125715 antihistaminic agent Drugs 0.000 claims description 6
125000003884 phenylalkyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000005606 carbostyryl group Chemical group 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 301
239000013078 crystal Substances 0.000 description 270
150000001875 compounds Chemical class 0.000 description 217
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
238000006243 chemical reaction Methods 0.000 description 111
235000019441 ethanol Nutrition 0.000 description 108
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 105
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 78
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 49
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
239000000243 solution Substances 0.000 description 42
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 38
239000002904 solvent Substances 0.000 description 35
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
238000001953 recrystallisation Methods 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 30
238000001914 filtration Methods 0.000 description 27
238000004821 distillation Methods 0.000 description 26
239000000203 mixture Substances 0.000 description 25
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
238000000034 method Methods 0.000 description 24
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 23
125000004193 piperazinyl group Chemical group 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 22
241000699670 Mus sp. Species 0.000 description 20
238000010992 reflux Methods 0.000 description 20
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
150000007514 bases Chemical class 0.000 description 17
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 16
239000010410 layer Substances 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
230000002140 halogenating effect Effects 0.000 description 14
235000011121 sodium hydroxide Nutrition 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000012442 inert solvent Substances 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
238000003756 stirring Methods 0.000 description 12
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 11
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 11
229960001340 histamine Drugs 0.000 description 11
239000007858 starting material Substances 0.000 description 11
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
235000009518 sodium iodide Nutrition 0.000 description 10
239000008096 xylene Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
230000037396 body weight Effects 0.000 description 9
238000001816 cooling Methods 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
235000011181 potassium carbonates Nutrition 0.000 description 8
235000011118 potassium hydroxide Nutrition 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
235000017550 sodium carbonate Nutrition 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 7
TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
241000699666 Mus <mouse, genus> Species 0.000 description 7
239000007924 injection Substances 0.000 description 7
238000002347 injection Methods 0.000 description 7
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
244000215068 Acacia senegal Species 0.000 description 6
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 6
229920000084 Gum arabic Polymers 0.000 description 6
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 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
235000010489 acacia gum Nutrition 0.000 description 6
239000000205 acacia gum Substances 0.000 description 6
239000008103 glucose Substances 0.000 description 6
235000001727 glucose Nutrition 0.000 description 6
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
239000008101 lactose Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
239000008107 starch Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 4
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000007884 disintegrant Substances 0.000 description 4
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
238000009472 formulation Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000463 material Substances 0.000 description 4
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
210000000813 small intestine Anatomy 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 3
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
JHWVAWUKMRXHCM-UHFFFAOYSA-N 5-(3-chloropropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCCCCl JHWVAWUKMRXHCM-UHFFFAOYSA-N 0.000 description 3
NQCVIXJSFZMILF-UHFFFAOYSA-N 7-(3-chloropropoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=CC(OCCCCl)=CC=C21 NQCVIXJSFZMILF-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
206010002091 Anaesthesia Diseases 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
244000060011 Cocos nucifera Species 0.000 description 3
235000013162 Cocos nucifera Nutrition 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
230000037005 anaesthesia Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
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 3
239000011230 binding agent Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
235000014121 butter Nutrition 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 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
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
229960003878 haloperidol Drugs 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000003326 hypnotic agent Substances 0.000 description 3
230000000147 hypnotic effect Effects 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000002504 physiological saline solution Substances 0.000 description 3
239000006187 pill Substances 0.000 description 3
239000011736 potassium bicarbonate Substances 0.000 description 3
235000015497 potassium bicarbonate Nutrition 0.000 description 3
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002304 perfume Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
238000001050 pharmacotherapy Methods 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
DHAVNRJKBRMQMN-UHFFFAOYSA-N propan-2-ol;1h-quinolin-2-one Chemical compound CC(C)O.C1=CC=C2NC(=O)C=CC2=C1 DHAVNRJKBRMQMN-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001528 ptotic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
206010041232 sneezing Diseases 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000013599 spices Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000006794 tachycardia 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
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000035922 thirst Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
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
150000004684 trihydrates Chemical class 0.000 description 1
230000002792 vascular Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
- 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
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Anesthesiology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SE7902794A 1978-03-30 1979-03-29 Karbostyrilderivat SE434945B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3778378A JPS54130587A (en)	1978-03-30	1978-03-30	Carbostyryl derivative

Publications (2)

Publication Number	Publication Date
SE7902794L SE7902794L (sv)	1979-10-01
SE434945B true SE434945B (sv)	1984-08-27

Family

ID=12507080

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7902794A SE434945B (sv)	1978-03-30	1979-03-29	Karbostyrilderivat

Country Status (21)

Country	Link
US (2)	US4734416A (fr)
JP (1)	JPS54130587A (fr)
AT (1)	AT376432B (fr)
AU (1)	AU515531B2 (fr)
BE (1)	BE875174A (fr)
CA (1)	CA1117110A (fr)
CH (2)	CH641455A5 (fr)
DE (2)	DE2953723C2 (fr)
DK (1)	DK158225C (fr)
ES (4)	ES479134A1 (fr)
FI (1)	FI70704C (fr)
FR (1)	FR2421174A1 (fr)
GB (1)	GB2017701B (fr)
IT (1)	IT1119284B (fr)
MX (1)	MX5862E (fr)
NL (1)	NL183189C (fr)
NO (1)	NO151321C (fr)
PT (1)	PT69422A (fr)
SE (1)	SE434945B (fr)
SU (2)	SU1140687A3 (fr)
ZA (1)	ZA791516B (fr)

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1978
- 1978-03-30 JP JP3778378A patent/JPS54130587A/ja active Granted
1979
- 1979-03-27 DE DE2953723A patent/DE2953723C2/de not_active Expired
- 1979-03-27 CA CA000324227A patent/CA1117110A/fr not_active Expired
- 1979-03-27 DE DE2912105A patent/DE2912105C2/de not_active Expired
- 1979-03-28 FI FI791034A patent/FI70704C/fi not_active IP Right Cessation
- 1979-03-28 US US06/024,602 patent/US4734416A/en not_active Expired - Lifetime
- 1979-03-28 AU AU45480/79A patent/AU515531B2/en not_active Expired
- 1979-03-29 DK DK128679A patent/DK158225C/da not_active IP Right Cessation
- 1979-03-29 CH CH295379A patent/CH641455A5/de not_active IP Right Cessation
- 1979-03-29 FR FR7907863A patent/FR2421174A1/fr active Granted
- 1979-03-29 SE SE7902794A patent/SE434945B/sv not_active IP Right Cessation
- 1979-03-29 NO NO791049A patent/NO151321C/no unknown
- 1979-03-29 AT AT0235179A patent/AT376432B/de not_active IP Right Cessation
- 1979-03-29 BE BE0/194281A patent/BE875174A/fr not_active IP Right Cessation
- 1979-03-29 SU SU792745704A patent/SU1140687A3/ru active
- 1979-03-30 ZA ZA791516A patent/ZA791516B/xx unknown
- 1979-03-30 NL NLAANVRAGE7902514,A patent/NL183189C/xx not_active IP Right Cessation
- 1979-03-30 PT PT69422A patent/PT69422A/pt unknown
- 1979-03-30 IT IT67674/79A patent/IT1119284B/it active
- 1979-03-30 GB GB7911155A patent/GB2017701B/en not_active Expired
- 1979-03-30 ES ES479134A patent/ES479134A1/es not_active Expired
- 1979-03-30 MX MX797848U patent/MX5862E/es unknown
- 1979-12-17 ES ES486992A patent/ES486992A1/es not_active Expired
- 1979-12-17 ES ES486990A patent/ES486990A1/es not_active Expired
- 1979-12-17 ES ES486991A patent/ES486991A1/es not_active Expired
1981
- 1981-09-08 SU SU813328599A patent/SU1232144A3/ru active
1982
- 1982-03-26 CH CH190082A patent/CH641350A5/de not_active IP Right Cessation
1987
- 1987-03-12 US US07/025,193 patent/US4824840A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO151321B (no)	1984-12-10
IT1119284B (it)	1986-03-10
ZA791516B (en)	1980-04-30
SU1140687A3 (ru)	1985-02-15
CA1117110A (fr)	1982-01-26
NL183189C (nl)	1988-08-16
AU515531B2 (en)	1981-04-09
FI791034A7 (fi)	1979-10-01
ES479134A1 (es)	1980-06-16
FR2421174B1 (fr)	1982-11-19
IT7967674A0 (it)	1979-03-30
ES486991A1 (es)	1980-10-01
ATA235179A (de)	1984-04-15
JPS54130587A (en)	1979-10-09
AT376432B (de)	1984-11-26
NL7902514A (nl)	1979-10-02
FR2421174A1 (fr)	1979-10-26
DK158225B (da)	1990-04-16
GB2017701A (en)	1979-10-10
JPS6223750B2 (fr)	1987-05-25
BE875174A (fr)	1979-10-01
PT69422A (en)	1979-04-01
DK158225C (da)	1990-09-17
NO151321C (no)	1985-03-20
ES486992A1 (es)	1980-10-01
GB2017701B (en)	1983-03-16
US4824840A (en)	1989-04-25
MX5862E (es)	1984-08-13
CH641350A5 (de)	1984-02-29
US4734416A (en)	1988-03-29
SU1232144A3 (ru)	1986-05-15
SE7902794L (sv)	1979-10-01
DE2912105C2 (de)	1985-08-29
DK128679A (da)	1979-10-26
DE2912105A1 (de)	1979-10-11
CH641455A5 (de)	1984-02-29
NO791049L (no)	1979-10-02
DE2953723C2 (de)	1989-01-12
ES486990A1 (es)	1980-10-01
FI70704C (fi)	1986-10-06
AU4548079A (en)	1979-10-04
FI70704B (fi)	1986-06-26

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