CH623039A5 - - Google Patents

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Info

Publication number: CH623039A5
Authority: CH; Switzerland
Prior art keywords: formula; mixture; dihydroxy; trimethoxybenzyl; solution
Prior art date: 1974-11-20

Application number

CH606580A

Other languages

German (de)

English (en)

Inventor

Muneyoshi Ikezaki

Kunihiko Irie

Norihide Umino

Katsuo Ikezawa

Masanori Sato

Original Assignee

Tanabe Seiyaku Co

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.)

1974-11-20

Filing date

1980-08-11

Publication date

1981-05-15

1980-08-11 Application filed by Tanabe Seiyaku Co filed Critical Tanabe Seiyaku Co

1981-05-15 Publication of CH623039A5 publication Critical patent/CH623039A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
239000012298 atmosphere Substances 0.000 claims description 5
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 4
229910003446 platinum oxide Inorganic materials 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 23
239000000243 solution Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 15
-1 3,5-dibenzyloxybenzyl Chemical group 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
229910052783 alkali metal Inorganic materials 0.000 description 8
DYPPKOJVTFEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-5,7-diol Chemical class C1CNCC2=CC(O)=CC(O)=C21 DYPPKOJVTFEWKK-UHFFFAOYSA-N 0.000 description 7
229940124630 bronchodilator Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
230000003449 preventive effect Effects 0.000 description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 3
YEPUBSSZBRVJGB-UHFFFAOYSA-N 5,7-bis(phenylmethoxy)isoquinoline Chemical class C=1C=CC=CC=1COC(C=C1C=NC=CC1=1)=CC=1OCC1=CC=CC=C1 YEPUBSSZBRVJGB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 3
OJEBXSFMIBPGCR-UHFFFAOYSA-N 1-[(3,4,5-trimethoxyphenyl)methyl]isoquinoline-5,7-diol Chemical compound COC1=C(OC)C(OC)=CC(CC=2C3=CC(O)=CC(O)=C3C=CN=2)=C1 OJEBXSFMIBPGCR-UHFFFAOYSA-N 0.000 description 2
CHUAMRVJSRBRHT-UHFFFAOYSA-N 3,5-bis(phenylmethoxy)benzaldehyde Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C=O)=CC=1OCC1=CC=CC=C1 CHUAMRVJSRBRHT-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
VFRDRGMLKZVHEP-UHFFFAOYSA-N 5,7-bis(phenylmethoxy)-1-[(3,4,5-trimethoxyphenyl)methyl]isoquinoline Chemical compound COC1=C(OC)C(OC)=CC(CC=2C3=CC(OCC=4C=CC=CC=4)=CC(OCC=4C=CC=CC=4)=C3C=CN=2)=C1 VFRDRGMLKZVHEP-UHFFFAOYSA-N 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
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 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000006796 Pomeranz-Fritsch reaction Methods 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
230000007885 bronchoconstriction Effects 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000010779 crude oil Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000004800 hydroisoquinoline derivatives Chemical class 0.000 description 2
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
UNZCEFQEAOOUMC-UHFFFAOYSA-N 1-[3,5-bis(phenylmethoxy)phenyl]-n-(2,2-diethoxyethyl)methanimine Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C=NCC(OCC)OCC)=CC=1OCC1=CC=CC=C1 UNZCEFQEAOOUMC-UHFFFAOYSA-N 0.000 description 1
UJTKOZCOKPPSLR-UHFFFAOYSA-N 1-benzyl-3,4,5-trimethoxyisoquinoline Chemical compound C=12C=CC=C(OC)C2=C(OC)C(OC)=NC=1CC1=CC=CC=C1 UJTKOZCOKPPSLR-UHFFFAOYSA-N 0.000 description 1
HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
PDZYOCOHQGFKLC-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)acetaldehyde Chemical compound COC1=CC(CC=O)=CC(OC)=C1OC PDZYOCOHQGFKLC-UHFFFAOYSA-N 0.000 description 1
OZLPUNFFCJDMJD-UHFFFAOYSA-N 2-[2,3-bis[2-(triethylammonio)ethoxy]phenoxy]ethyl-triethylammonium Chemical compound CC[N+](CC)(CC)CCOC1=CC=CC(OCC[N+](CC)(CC)CC)=C1OCC[N+](CC)(CC)CC OZLPUNFFCJDMJD-UHFFFAOYSA-N 0.000 description 1
VBRHKASXOHBFIV-UHFFFAOYSA-N 2-benzoyl-5,7-bis(phenylmethoxy)-1h-isoquinoline-1-carbonitrile Chemical compound C=1C=CC=CC=1C(=O)N(C(C1=CC(OCC=2C=CC=CC=2)=C2)C#N)C=CC1=C2OCC1=CC=CC=C1 VBRHKASXOHBFIV-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
DOAJPCANOVHQEZ-UHFFFAOYSA-N 5,7-bis(phenylmethoxy)quinoline Chemical compound C(C1=CC=CC=C1)OC1=C2C=CC=NC2=CC(=C1)OCC1=CC=CC=C1 DOAJPCANOVHQEZ-UHFFFAOYSA-N 0.000 description 1
XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 description 1
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 1
108010010803 Gelatin Proteins 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
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
231100000111 LD50 Toxicity 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000002585 base Substances 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
239000011230 binding agent Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000004044 bronchoconstricting agent Substances 0.000 description 1
230000003435 bronchoconstrictive effect Effects 0.000 description 1
230000003182 bronchodilatating effect Effects 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
229940109239 creatinine Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000002012 dioxanes Chemical class 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
229960003054 gallamine Drugs 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
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
MBTGQYUUQPILKD-UHFFFAOYSA-N n-[[3,5-bis(phenylmethoxy)phenyl]methyl]-2,2-diethoxyethanamine Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(CNCC(OCC)OCC)=CC=1OCC1=CC=CC=C1 MBTGQYUUQPILKD-UHFFFAOYSA-N 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
239000008023 pharmaceutical filler Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
239000007787 solid 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
238000003756 stirring Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000003526 tetrahydroisoquinolines Chemical class 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

CH606580A 1974-11-20 1980-08-11 CH623039A5 (zh)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP49134734A JPS5247474B2 (zh)	1974-11-20	1974-11-20

Publications (1)

Publication Number	Publication Date
CH623039A5 true CH623039A5 (zh)	1981-05-15

Family

ID=15135331

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1504875A CH621341A5 (zh)	1974-11-20	1975-11-20
CH606580A CH623039A5 (zh)	1974-11-20	1980-08-11

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH1504875A CH621341A5 (zh)	1974-11-20	1975-11-20

Country Status (12)

Country	Link
US (1)	US4054659A (zh)
JP (1)	JPS5247474B2 (zh)
BE (1)	BE835744A (zh)
CA (1)	CA1032541A (zh)
CH (2)	CH621341A5 (zh)
CS (1)	CS190503B2 (zh)
DK (1)	DK143197C (zh)
FR (1)	FR2291753A1 (zh)
GB (1)	GB1487457A (zh)
HU (1)	HU170648B (zh)
NL (1)	NL166469C (zh)
SE (1)	SE424638B (zh)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5817465B2 (ja) *	1977-09-02	1983-04-07	田辺製薬株式会社	テトラヒドロイソキノリン誘導体の製法
JPS5484035A (en) *	1977-12-16	1979-07-04	Tanabe Seiyaku Co Ltd	Anti-allergic agent
EP1023269A4 (en) *	1997-09-30	2001-06-27	Molecular Design Int	BETA3-ADRENORECEPTOR AGONISTS, AGONIST COMPOSITIONS AND METHODS OF USE
CA2435883A1 (en)	2001-01-26	2002-08-01	Sankyo Company, Limited	Benzylamine analogue
US6593341B2 (en)	2001-03-29	2003-07-15	Molecular Design International, Inc.	β3-adrenoreceptor agonists, agonist compositions and methods of making and using the same
US6596734B1 (en)	2002-10-11	2003-07-22	Molecular Design International, Inc.	Tetrahydroisoquinoline compounds for use as β3-adrenoreceptor agonists

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3873704A (en) *	1970-12-17	1975-03-25	Tanabe Seiyaku Co	Novel tetrahydroisoquinoline compounds in a pharmaceutical composition
JPS5734275B2 (zh) *	1973-07-30	1982-07-22

1974
- 1974-11-20 JP JP49134734A patent/JPS5247474B2/ja not_active Expired
1975
- 1975-10-29 DK DK487375A patent/DK143197C/da not_active IP Right Cessation
- 1975-10-30 US US05/627,259 patent/US4054659A/en not_active Expired - Lifetime
- 1975-10-30 GB GB44807/75A patent/GB1487457A/en not_active Expired
- 1975-11-18 CS CS757781A patent/CS190503B2/cs unknown
- 1975-11-18 CA CA239,977A patent/CA1032541A/en not_active Expired
- 1975-11-19 NL NL7513517.A patent/NL166469C/xx not_active IP Right Cessation
- 1975-11-19 SE SE7513013A patent/SE424638B/xx unknown
- 1975-11-19 HU HUTA1379A patent/HU170648B/hu unknown
- 1975-11-19 BE BE6045258A patent/BE835744A/xx not_active IP Right Cessation
- 1975-11-19 FR FR7535390A patent/FR2291753A1/fr active Granted
- 1975-11-20 CH CH1504875A patent/CH621341A5/de not_active IP Right Cessation
1980
- 1980-08-11 CH CH606580A patent/CH623039A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2291753B1 (zh)	1978-11-10
CS190503B2 (en)	1979-05-31
DE2551924B2 (de)	1977-05-26
CA1032541A (en)	1978-06-06
BE835744A (fr)	1976-03-16
HU170648B (zh)	1977-07-28
DE2551924A1 (de)	1976-05-26
SE424638B (sv)	1982-08-02
SE7513013L (sv)	1976-05-21
AU8671375A (en)	1977-03-17
US4054659A (en)	1977-10-18
CH621341A5 (zh)	1981-01-30
NL7513517A (nl)	1976-05-24
DK143197B (da)	1981-07-20
NL166469C (nl)	1981-08-17
DK143197C (da)	1981-11-23
FR2291753A1 (fr)	1976-06-18
JPS5170770A (zh)	1976-06-18
DK487375A (da)	1976-05-21
GB1487457A (en)	1977-09-28
NL166469B (nl)	1981-03-16
JPS5247474B2 (zh)	1977-12-02

Publication	Publication Date	Title
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
DE2243961C2 (zh)	1988-07-21
DE2345064C3 (de)	1979-10-25	4-Amino-2-<l,2r3,4-tetrahydroisochinolin-2 yl)-chinazolinderivate und diese enthaltende Arzneimittel
DE2901170C2 (zh)	1992-09-17
DE2105743A1 (en)	1972-08-31	2-(furylmethyl)-6,7-benzomorphans - useful as cns active agents
DE2062001C2 (de)	1986-10-16	1,2,3,4-Tetrahydro-4-phenylisochinolin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und pharmazeutisches Präparat
DE2305092C2 (zh)	1987-10-01
DE2108954A1 (en)	1972-09-07	2-(furylmethyl)-6,7-benzomorphans - useful as cns active agents
DE2261506A1 (de)	1973-06-28	Basische derivate von phenyl-1 alkanolen, ihre herstellung und diese enthaltende medikamente
EP0105210B1 (de)	1987-03-04	Isochinolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
DE2164619A1 (de)	1972-07-13	Neue 1,2,3,4-Tetrahydroisoichinolin-Derivate und Verfahren zu ihrer Herstellung
CH623039A5 (zh)	1981-05-15
EP0064685A1 (de)	1982-11-17	Dibenzo(de,g)chinolin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
CH668973A5 (de)	1989-02-15	Purin-derivate, ihre herstellung und sie enthaltende arzneimittel.
CH646970A5 (de)	1984-12-28	Hydroxyamino-eburnamin-derivate, diese verbindungen enthaltende arzneimittel sowie ein verfahren zu ihrer herstellung.
DE1961947C3 (de)	1974-10-31	Racemische und optisch aktive 1-(3,4,5-Trimethoxybenzyl)-6,7-dialkanoyloxy-l^S^-tetrahydroisochinoline
CH619952A5 (zh)	1980-10-31
US4016176A (en)	1977-04-05	Esters of 4-hydroxy-2,9-dioxatricyclo[4.3.1.03,7 ] decanes and processes for their production
DE1097996B (de)	1961-01-26	Verfahren zur Herstellung von Phenthiazinderivaten
DE2551924C3 (de)	1978-01-19	l-(3,43-Trimethoxybenzyl) -5,7dihydroxy-l,23,4-tetrahydroisochinolin, dessen Salze, Verfahren zu deren Herstellung und pharmazeutische Zubereitungen
DE2233088A1 (de)	1974-01-17	Benzomorphanderivate
CH639638A5 (de)	1983-11-30	Racemischer oder optisch aktiver alpha-(2,3,4-trimethoxyphenaethylaminomethyl)-2-hydroxybenzylalkohol und pharmazeutisch zulaessige saeureadditionssalze davon.
DE1470062A1 (de)	1969-05-08	Verfahren zur Herstellung von 1,2,3,6,7,11 b-Hexahydro-4 H-pyrazino-[2,1-a]-isochinolinen
DE2508251A1 (de)	1976-09-09	Neue derivate des indols, verfahren zu deren herstellung sowie diese enthaltende arzneimittel
CH638519A5 (de)	1983-09-30	2'-hydroxy-2-(5-isoxazolylmethyl)-6,7-benzomorphane, deren saeureadditionssalze und diese verbindungen enthaltende arzneimittel.

Legal Events

Date	Code	Title	Description
1986-07-31	PL	Patent ceased
2024-10-31	PL	Patent ceased