CA1064036A - Derives de la benzcycloamide - Google Patents

Derives de la benzcycloamide

Info

Publication number: CA1064036A
Authority: CA; Canada
Prior art keywords: dihydrocarbostyril; reaction; process according; hydrogen; ials
Prior art date: 1974-06-24
Legal status (The legal status 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 status listed.): Expired

Application number

CA315,114A

Other languages

English (en)

Inventor

Kimiaki Oka

Minoru Uchida

Kazuyuki Nakagawa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Otsuka Pharmaceutical Co Ltd

Original Assignee

Otsuka Pharmaceutical 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.)

1974-06-24

Filing date

1978-10-31

Publication date

1979-10-09

1974-06-24 Priority claimed from JP49072472A external-priority patent/JPS511480A/ja

1974-06-24 Priority claimed from JP49072473A external-priority patent/JPS511481A/ja

1974-07-05 Priority claimed from JP49077661A external-priority patent/JPS5182279A/ja

1974-07-05 Priority claimed from JP49077660A external-priority patent/JPS516970A/ja

1974-08-16 Priority claimed from JP49094376A external-priority patent/JPS5123271A/ja

1975-04-30 Priority claimed from JP50053027A external-priority patent/JPS51128977A/ja

1975-04-30 Priority claimed from JP50053028A external-priority patent/JPS51128978A/ja

1975-04-30 Priority claimed from JP50053026A external-priority patent/JPS51128976A/ja

1975-05-15 Priority claimed from JP50058135A external-priority patent/JPS51133284A/ja

1975-05-15 Priority claimed from JP50058134A external-priority patent/JPS51133283A/ja

1975-05-15 Priority claimed from JP50058128A external-priority patent/JPS51133277A/ja

1975-05-15 Priority claimed from JP50058129A external-priority patent/JPS51133278A/ja

1975-05-16 Priority claimed from JP50058874A external-priority patent/JPS51136677A/ja

1975-05-16 Priority claimed from JP50058872A external-priority patent/JPS604173B2/ja

1975-06-02 Priority claimed from JP50066729A external-priority patent/JPS51141864A/ja

1975-06-23 Priority claimed from CA75229940A external-priority patent/CA1048497A/fr

1978-10-31 Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd

1978-10-31 Priority to CA315,114A priority Critical patent/CA1064036A/fr

1979-10-09 Application granted granted Critical

1979-10-09 Publication of CA1064036A publication Critical patent/CA1064036A/fr

Status Expired legal-status Critical Current

Links

229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
150000002431 hydrogen Chemical group 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 106
238000006243 chemical reaction Methods 0.000 claims description 69
150000001875 compounds Chemical class 0.000 claims description 57
238000000034 method Methods 0.000 claims description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
230000008569 process Effects 0.000 claims description 30
-1 6-cyanomethoxy-3,4-dihydro-carbostyril Chemical compound 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
239000007858 starting material Substances 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
238000006460 hydrolysis reaction Methods 0.000 claims description 7
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 7
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
238000006136 alcoholysis reaction Methods 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
239000003377 acid catalyst Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
238000010932 ethanolysis reaction Methods 0.000 claims 6
QYEVFSONZNYCBJ-UHFFFAOYSA-N ethyl 2-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]acetate Chemical compound N1C(=O)CCC2=CC(OCC(=O)OCC)=CC=C21 QYEVFSONZNYCBJ-UHFFFAOYSA-N 0.000 claims 3
FZTXRPKCLIDQSI-UHFFFAOYSA-N ethyl 3-methyl-4-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]butanoate Chemical compound N1C(=O)CCC2=CC(OCC(C)CC(=O)OCC)=CC=C21 FZTXRPKCLIDQSI-UHFFFAOYSA-N 0.000 claims 3
HFUIGOFKSVEFSI-UHFFFAOYSA-N ethyl 2-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]propanoate Chemical compound N1C(=O)CCC2=CC(OC(C)C(=O)OCC)=CC=C21 HFUIGOFKSVEFSI-UHFFFAOYSA-N 0.000 claims 2
230000006203 ethylation Effects 0.000 claims 2
238000006200 ethylation reaction Methods 0.000 claims 2
VYZHZRBXFADZJA-UHFFFAOYSA-N 2-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]acetic acid Chemical compound N1C(=O)CCC2=CC(OCC(=O)O)=CC=C21 VYZHZRBXFADZJA-UHFFFAOYSA-N 0.000 claims 1
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 claims 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
230000000694 effects Effects 0.000 abstract description 4
229910052757 nitrogen Inorganic materials 0.000 abstract description 4
208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 4
206010014523 Embolism and thrombosis Diseases 0.000 abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
230000003449 preventive effect Effects 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract description 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
125000004434 sulfur atom Chemical group 0.000 abstract 1
239000000243 solution Substances 0.000 description 87
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
239000013078 crystal Substances 0.000 description 81
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
239000002904 solvent Substances 0.000 description 54
239000000203 mixture Substances 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
229960001701 chloroform Drugs 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
235000011121 sodium hydroxide Nutrition 0.000 description 26
229940083608 sodium hydroxide Drugs 0.000 description 26
239000003054 catalyst Substances 0.000 description 24
238000001914 filtration Methods 0.000 description 24
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 24
239000012295 chemical reaction liquid Substances 0.000 description 21
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
208000007536 Thrombosis Diseases 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
125000000217 alkyl group Chemical group 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
230000002776 aggregation Effects 0.000 description 13
238000004220 aggregation Methods 0.000 description 13
235000008504 concentrate Nutrition 0.000 description 13
239000012141 concentrate Substances 0.000 description 13
239000004567 concrete Substances 0.000 description 13
238000004821 distillation Methods 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
FVXYRXMYPXVHNY-UHFFFAOYSA-N 3-propoxy-3,4-dihydro-1H-quinolin-2-one Chemical compound C(CC)OC1C(NC2=CC=CC=C2C1)=O FVXYRXMYPXVHNY-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
235000011167 hydrochloric acid Nutrition 0.000 description 12
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 11
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 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
239000010410 layer Substances 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
239000011734 sodium Substances 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
239000008280 blood Substances 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
239000008096 xylene Substances 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
210000001772 blood platelet Anatomy 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
201000010099 disease Diseases 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
235000009518 sodium iodide Nutrition 0.000 description 8
102000008186 Collagen Human genes 0.000 description 7
108010035532 Collagen Proteins 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
229920001436 collagen Polymers 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000007788 liquid Substances 0.000 description 7
229960003975 potassium Drugs 0.000 description 7
239000011591 potassium Substances 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 6
XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
239000000010 aprotic solvent Substances 0.000 description 6
210000004204 blood vessel Anatomy 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
238000011161 development Methods 0.000 description 6
230000018109 developmental process Effects 0.000 description 6
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
UTTJAIFHRUAFED-UHFFFAOYSA-N 5-hydroxy-3,4-dihydro-2(1h)-quinolinone Chemical compound N1C(=O)CCC2=C1C=CC=C2O UTTJAIFHRUAFED-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
229960005335 propanol Drugs 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
235000017550 sodium carbonate Nutrition 0.000 description 5
239000007787 solid Substances 0.000 description 5
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
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
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
150000007514 bases Chemical class 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229910017052 cobalt Inorganic materials 0.000 description 4
239000010941 cobalt Substances 0.000 description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
239000000306 component Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
CSRDIQYESGAEPH-UHFFFAOYSA-N ethyl 2-[(2-oxo-3,4-dihydro-1h-quinolin-5-yl)oxy]acetate Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(=O)OCC CSRDIQYESGAEPH-UHFFFAOYSA-N 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
239000008101 lactose Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229910001511 metal iodide Inorganic materials 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
235000011118 potassium hydroxide Nutrition 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 3
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 3
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210000000709 aorta Anatomy 0.000 description 1
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229910001863 barium hydroxide Chemical class 0.000 description 1
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
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230000017531 blood circulation Effects 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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238000006482 condensation reaction Methods 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
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150000001924 cycloalkanes Chemical class 0.000 description 1
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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
230000003111 delayed effect Effects 0.000 description 1
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206010012601 diabetes mellitus Diseases 0.000 description 1
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230000037213 diet Effects 0.000 description 1
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DXBULVYHTICWKT-UHFFFAOYSA-N ethyl 6-bromohexanoate Chemical compound CCOC(=O)CCCCCBr DXBULVYHTICWKT-UHFFFAOYSA-N 0.000 description 1
238000011049 filling Methods 0.000 description 1
235000011194 food seasoning agent Nutrition 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
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229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
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239000008240 homogeneous mixture Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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230000005764 inhibitory process Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
208000023589 ischemic disease Diseases 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000000463 material Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000010446 mirabilite Substances 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical group [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
150000004672 propanoic acids Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
GKTWIJVDNVTXCV-UHFFFAOYSA-N propyl 5-bromopentanoate Chemical compound CCCOC(=O)CCCCBr GKTWIJVDNVTXCV-UHFFFAOYSA-N 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
230000007575 pulmonary infarction Effects 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
229940098221 silver cyanide Drugs 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000011146 sterile filtration Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
DGCFCIXSJPYNLX-UHFFFAOYSA-N trichloromethylsulfonyl trichloromethanesulfonate Chemical compound ClC(Cl)(Cl)S(=O)(=O)OS(=O)(=O)C(Cl)(Cl)Cl DGCFCIXSJPYNLX-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
239000012000 urushibara nickel Substances 0.000 description 1
238000013022 venting Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA315,114A 1974-06-24 1978-10-31 Derives de la benzcycloamide Expired CA1064036A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA315,114A CA1064036A (fr)	1974-06-24	1978-10-31	Derives de la benzcycloamide

Applications Claiming Priority (17)

Application Number	Priority Date	Filing Date	Title
JP49072473A JPS511481A (ja)	1974-06-24	1974-06-24	Karubokishiarukokishi 3*44 jihidorokarubosuchirirujudotaino seizoho
JP49072472A JPS511480A (ja)	1974-06-24	1974-06-24	Etokishikaruboniruarukokishi 3*44 jihidorokarubosuchirirujudotaino seizoho
JP49077660A JPS516970A (en)	1974-07-05	1974-07-05	Shianoetokishi 3*44 jihidorokarubosuchirirujudotaino seizoho
JP49077661A JPS5182279A (en)	1974-07-05	1974-07-05	Karubokishetokishi 3*44 jihidorokarubosuchirirujudotainoseizoho
JP49094376A JPS5123271A (ja)	1974-08-16	1974-08-16	Karubamoiruarukokishi 3*44 jihidorokarubosuchirirujudotaiseizoho
JP50053028A JPS51128978A (en)	1975-04-30	1975-04-30	Process for preparing carbostyril derivatives
JP50053027A JPS51128977A (en)	1975-04-30	1975-04-30	Process for preparing carbostyril derivatives
JP50053026A JPS51128976A (en)	1975-04-30	1975-04-30	Process for preparing carbostyril derivatives
JP50058135A JPS51133284A (en)	1975-05-15	1975-05-15	A process for preparing carbostyril derivatives
JP50058134A JPS51133283A (en)	1975-05-15	1975-05-15	A process for preparing carbostyril derivatives
JP50058128A JPS51133277A (en)	1975-05-15	1975-05-15	A process for preparing novel carbostyril derivatives
JP50058129A JPS51133278A (en)	1975-05-15	1975-05-15	A process for preparing novel carbostyril derivatives
JP50058874A JPS51136677A (en)	1975-05-16	1975-05-16	Process for preparation of carbostyril derivatives
JP50058872A JPS604173B2 (ja)	1975-05-16	1975-05-16	カルボスチリル誘導体の製法
JP50066729A JPS51141864A (en)	1975-06-02	1975-06-02	Process for preparing oxyindole derivatives.
CA75229940A CA1048497A (fr)	1974-06-24	1975-06-23	Derives de benzocyclamide
CA315,114A CA1064036A (fr)	1974-06-24	1978-10-31	Derives de la benzcycloamide

Publications (1)

Publication Number	Publication Date
CA1064036A true CA1064036A (fr)	1979-10-09

Family

ID=34831598

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA315,114A Expired CA1064036A (fr)	1974-06-24	1978-10-31	Derives de la benzcycloamide

Country Status (1)

Country	Link
CA (1)	CA1064036A (fr)

1978
- 1978-10-31 CA CA315,114A patent/CA1064036A/fr not_active Expired

Publication	Publication Date	Title
CA1048497A (fr)	1979-02-13	Derives de benzocyclamide
US4313947A (en)	1982-02-02	Platelet aggregation inhibiting 2-oxyindoles, their compositions and method of use
US4277479A (en)	1981-07-07	Tetrazolylalkoxycarbostyril derivatives and pharmaceutical compositions containing them
CA1087205A (fr)	1980-10-07	Acides 2-amino-3-(5-et 6-)benzoylphenylacetiques, leurs esters et sels metalliques
EP0593478B1 (fr)	1995-12-06	Antagonistes de leukotriene b 4
IE46852B1 (en)	1983-10-05	Novel carbostyril derivatives
US3853923A (en)	1974-12-10	2-substituted-(2-hydroxy-3-lower alkaminopropoxy)-benzofurans
PL119501B1 (en)	1982-01-30	Process for manufacturing novel,condensed pyrimidine derivatives pirimidina
US5248693A (en)	1993-09-28	Acetylene compounds and pharmaceutical compositions and methods of using the same
CA1084918A (fr)	1980-09-02	Obtention de 5,11-dihydro-6h-pyrido 2,3,b - 1,4 benzoidazepin-6-ones substituees en 11; produits pharmaceutiques qui les contiennent
EP0053789B1 (fr)	1985-03-27	Dérivés de 2-pyridinecarboxamide, leur procédé de préparation et une composition pharmaceutique utilisable comme agent anti-allergique
US3843663A (en)	1974-10-22	1,8-naphthyridine compounds
CA1064036A (fr)	1979-10-09	Derives de la benzcycloamide
US4344957A (en)	1982-08-17	Benz-acyl-benzimidazole derivatives and antiallergic compositions
EP0156331A2 (fr)	1985-10-02	Dérivés de benzofuranne, procédé pour leur préparation et agents antihypertensifs les contenant
EP0194686B1 (fr)	1989-12-20	Dérivés de la pyrazine
EP0350990A1 (fr)	1990-01-17	Dérivés de pyridazinone
US3984429A (en)	1976-10-05	Pharmaceutically active compounds
EP0326379A2 (fr)	1989-08-02	Agent thérapeutique pour les maladies du foie et dérivés de la pipérazine
US3984534A (en)	1976-10-05	Tetrazolyl anthraquinones for inhibiting the release of spasmogen mediators
US3962262A (en)	1976-06-08	1,8-naphthyridine compounds
US4574128A (en)	1986-03-04	5-(4-Chloro-3-sulfamoylbenzoyl)-2,3-dihydro-2-benzofurancarboxylic acids and their compositions having diuretic, saluretic and uricosuric activity
JPH05506440A (ja)	1993-09-22	アルコキシ置換ジヒドロベンゾピラン―２―カルボン酸およびその誘導体
US3992539A (en)	1976-11-16	S-triazolo-[3,4-a]isoquinolines in treating inflammatory disorders
EP0536400A1 (fr)	1993-04-14	Derive de tetrazole et medicament