PH26903A - Tetrahydronaphthalene derivatives - Google Patents

Tetrahydronaphthalene derivatives Download PDF

Info

Publication number: PH26903A
Authority: PH; Philippines
Prior art keywords: fluoro; tetrahydro; isopropyl; methyl; compounds
Prior art date: 1989-03-20

Application number

PH40216A

Other languages

English (en)

Inventor

Urs Dr Hengartner

Henri Dr Ramuz

Original Assignee

Hoffmann La Roche

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.)

1989-03-20

Filing date

1990-03-16

Publication date

1992-12-03

1990-03-16 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1992-12-03 Publication of PH26903A publication Critical patent/PH26903A/en

Links

CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 40
-1 methylenedioxy Chemical group 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
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 claims description 22
239000002253 acid Substances 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
RWIUTHWKQHRQNP-ZDVGBALWSA-N (9e,12e)-n-(1-phenylethyl)octadeca-9,12-dienamide Chemical compound CCCCC\C=C\C\C=C\CCCCCCCC(=O)NC(C)C1=CC=CC=C1 RWIUTHWKQHRQNP-ZDVGBALWSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 26
229950011260 betanaphthol Drugs 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 13
235000019198 oils Nutrition 0.000 description 13
238000004519 manufacturing process Methods 0.000 description 12
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000002775 capsule Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000000454 talc Substances 0.000 description 8
229910052623 talc Inorganic materials 0.000 description 8
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235000019759 Maize starch Nutrition 0.000 description 7
239000003814 drug Substances 0.000 description 7
238000002347 injection Methods 0.000 description 7
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235000019359 magnesium stearate Nutrition 0.000 description 7
238000000034 method Methods 0.000 description 7
229930000680 A04AD01 - Scopolamine Natural products 0.000 description 6
STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 6
STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
230000002490 cerebral effect Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 6
229960002646 scopolamine Drugs 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
235000011167 hydrochloric acid Nutrition 0.000 description 5
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239000000546 pharmaceutical excipient Substances 0.000 description 5
230000002265 prevention Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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 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
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 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
239000011230 binding agent Substances 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
230000003920 cognitive function Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000001828 Gelatine Substances 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229920003081 Povidone K 30 Polymers 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000006260 foam Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000006403 short-term memory Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
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150000001298 alcohols Chemical class 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229960003677 chloroquine Drugs 0.000 description 2
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 2
239000000824 cytostatic agent Substances 0.000 description 2
230000001085 cytostatic effect Effects 0.000 description 2
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239000008298 dragée Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 2
239000003925 fat Substances 0.000 description 2
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150000002367 halogens Chemical group 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
229940041476 lactose 100 mg Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
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201000004792 malaria Diseases 0.000 description 2
RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 2
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CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
230000003285 pharmacodynamic effect Effects 0.000 description 2
229940117803 phenethylamine Drugs 0.000 description 2
230000008569 process Effects 0.000 description 2
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239000007787 solid Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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DEGWMPOIXJTKLT-CYBMUJFWSA-N (1r)-6-fluoro-1-propan-2-yl-3,4-dihydro-1h-naphthalen-2-one Chemical compound FC1=CC=C2[C@@H](C(C)C)C(=O)CCC2=C1 DEGWMPOIXJTKLT-CYBMUJFWSA-N 0.000 description 1
YBQLHBYGMUXCEW-SNVBAGLBSA-N (2r)-2-(4-fluorophenyl)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)C1=CC=C(F)C=C1 YBQLHBYGMUXCEW-SNVBAGLBSA-N 0.000 description 1
FXINLCYHYNFBQX-UHFFFAOYSA-N 2-(2-fluoro-3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1F FXINLCYHYNFBQX-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
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125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 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
239000000872 buffer Substances 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000000546 chi-square test Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
206010013932 dyslexia Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000036541 health Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000008011 inorganic excipient Substances 0.000 description 1
230000035987 intoxication Effects 0.000 description 1
231100000566 intoxication Toxicity 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000015654 memory Effects 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
GLBUZFYJIIWCFB-UHFFFAOYSA-N propanethioyl chloride Chemical compound CCC(Cl)=S GLBUZFYJIIWCFB-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
208000027491 vestibular disease Diseases 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/25—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/24—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/48—Halogenated derivatives
- C07C35/52—Alcohols with a condensed ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Tropical Medicine & Parasitology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

PH40216A 1989-03-20 1990-03-16 Tetrahydronaphthalene derivatives PH26903A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH107489		1989-03-20

Publications (1)

Publication Number	Publication Date
PH26903A true PH26903A (en)	1992-12-03

Family

ID=4201845

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH40216A PH26903A (en)	1989-03-20	1990-03-16	Tetrahydronaphthalene derivatives

Country Status (15)

Country	Link
US (1)	US5120759A (pt)
EP (1)	EP0388739A1 (pt)
JP (1)	JPH02279660A (pt)
KR (1)	KR900014306A (pt)
AU (1)	AU5140390A (pt)
CA (1)	CA2011461A1 (pt)
FI (1)	FI901363A7 (pt)
HU (1)	HUT58042A (pt)
IL (1)	IL93750A0 (pt)
MC (1)	MC2105A1 (pt)
NO (1)	NO901266L (pt)
PH (1)	PH26903A (pt)
PT (1)	PT93504A (pt)
YU (1)	YU53490A (pt)
ZA (1)	ZA901926B (pt)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5910606A (en) *	1996-01-31	1999-06-08	Hoffmann-La Roche Inc.	Process for making α,β-unsaturated carboxylic acids
US5808088A (en) *	1997-04-30	1998-09-15	Roche Colorado Corporation	Preparation of mibefradil via an acetamide anion
US5811556A (en) *	1997-04-30	1998-09-22	Roche Colorado Corporation	Preparation of mibefradil via a naphthalenylacetic acid
US5811557A (en) *	1997-04-30	1998-09-22	Roche Colorado Corporation	Preparation of mibefradil via an acetonitrile anion
SI2152670T1 (sl)	2007-04-27	2014-04-30	Actelion Pharmaceuticals Ltd.	Premoščene šestčlenske obročne spojine
WO2010046729A2 (en) *	2008-10-23	2010-04-29	Actelion Pharmaceuticals Ltd	Tetrahydronaphthalene compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5896045A (ja) *	1981-11-30	1983-06-07	Sumitomo Chem Co Ltd	新規なジフエニルアルカノアミン誘導体およびその製造法
NZ213651A (en) *	1984-10-11	1989-07-27	Hoffmann La Roche	Tetrahydronapthalene derivatives and medicaments
CA1319144C (en) *	1986-11-14	1993-06-15	Quirico Branca	Tetrahydronaphthalene derivatives

1990
- 1990-03-05 CA CA002011461A patent/CA2011461A1/en not_active Abandoned
- 1990-03-09 EP EP90104562A patent/EP0388739A1/de not_active Withdrawn
- 1990-03-13 ZA ZA901926A patent/ZA901926B/xx unknown
- 1990-03-14 HU HU901556A patent/HUT58042A/hu unknown
- 1990-03-14 IL IL93750A patent/IL93750A0/xx unknown
- 1990-03-15 MC MC902118A patent/MC2105A1/fr unknown
- 1990-03-16 PH PH40216A patent/PH26903A/en unknown
- 1990-03-16 AU AU51403/90A patent/AU5140390A/en not_active Abandoned
- 1990-03-19 JP JP2067385A patent/JPH02279660A/ja active Pending
- 1990-03-19 FI FI901363A patent/FI901363A7/fi not_active IP Right Cessation
- 1990-03-19 KR KR1019900003627A patent/KR900014306A/ko not_active Withdrawn
- 1990-03-19 YU YU00534/90A patent/YU53490A/xx unknown
- 1990-03-19 NO NO90901266A patent/NO901266L/no unknown
- 1990-03-19 PT PT93504A patent/PT93504A/pt not_active Application Discontinuation
1991
- 1991-04-23 US US07/690,408 patent/US5120759A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FI901363A7 (fi)	1990-09-21
AU5140390A (en)	1990-11-15
IL93750A0 (en)	1990-12-23
MC2105A1 (fr)	1991-03-11
HU901556D0 (en)	1990-06-28
NO901266L (no)	1990-09-21
PT93504A (pt)	1990-11-07
ZA901926B (en)	1990-11-28
CA2011461A1 (en)	1990-09-20
US5120759A (en)	1992-06-09
NO901266D0 (no)	1990-03-19
HUT58042A (en)	1992-01-28
KR900014306A (ko)	1990-10-23
FI901363A0 (fi)	1990-03-19
EP0388739A1 (de)	1990-09-26
YU53490A (en)	1991-10-31
JPH02279660A (ja)	1990-11-15

Publication	Publication Date	Title
US4579854A (en)	1986-04-01	Bronchodilating 8-hydroxy-5-{(1R)-1-hydroxy-2-[N-((1R)-2-(p-methoxyphenyl)-1-methylethyl)-amino]ethyl} carbostyril
EP0335375B1 (en)	1993-06-09	Antihyperlipidemic and antiatherosclerotic compounds and compositions
NZ212856A (en)	1988-05-30	Glutarimide derivatives and pharmaceutical compositions
IE41528B1 (en)	1980-01-30	Benzomorphanes and derivatives and pharmaceutical compositions containing the same
AU2009201233B2 (en)	2012-07-05	Kappa-opioid receptor agonist comprising 2-phenylbenzothiazoline derivative
CA1287636C (en)	1991-08-13	Tetrahydronaphthalene derivatives
NZ192175A (en)	1984-05-31	Preparation of dextrorotatory trans 4a,9b-2-substituted-5--aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido-(4,3-b)indoles
US5120759A (en)	1992-06-09	Tetrahydronaphthalene derivatives for improving short-term memory
EP0175525B1 (en)	1990-05-23	7-[2-(Dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones
EP0406739A2 (en)	1991-01-09	Piperidine derivative, method for preparation thereof, and a pharmaceutical composition comprising the same
CA1327799C (en)	1994-03-15	Piperazinecarboxylic acid, its preparation and pharmaceutical compositions containing it
CA1142516A (en)	1983-03-08	10,11-dihydro-5h-dibenzo(a,d) cyclohepten-5,10-imines
EP0113910B1 (en)	1989-10-11	Isocarbostyril derivatives, processes for their preparation and pharmaceutical compositions containing them
EP0146155B1 (en)	1988-04-06	Ether of n-propanolamine derivative
EP0116268B1 (en)	1988-06-08	Novel quinazolinone derivative, a process for preparing the same and a pharmaceutical composition
IL43218A (en)	1977-05-31	2-n-phenyl-n-aminoalkyl-aminoindanes their preparation and pharmaceutical compositions containing them
NZ195688A (en)	1984-09-28	1-(8-quinolyl)-2-pyrrolidinone and pharmaceutical compositions
CA1243033A (en)	1988-10-11	Process for preparing 4-¬2- (dialkylamino)ethyl\|isatins
US3539642A (en)	1970-11-10	2-phenyl-2-(1-naphthyl)acetamides
IE840512L (en)	1984-09-03	Benzamide derivatives
US4003930A (en)	1977-01-18	2,3-Trans-5-[3-(amino)-2-hydroxy-propoxy]-1,2,3,4-tetrahydro-3-(or 2)-amino-2-(or 3)-hydroxy-naphthalenes and salts thereof
US4104402A (en)	1978-08-01	5,6-Dihydroxy aminotetralol compounds
FI58326C (fi)	1981-01-12	Foerfarande foer framstaellning av som beta-adrenergiskt stimulerande medel anvaendbara alfa-aminometyl-4-hydroksi-3-metylsulfonyl-metylbensylalkoholer
US3952050A (en)	1976-04-20	Cyclopent [a] indene compounds
CA1259074A (en)	1989-09-05	Carbostyril derivative and process for preparing same