RU2033991C1 - Производные аминоалкилбензола или их фармацевтически приемлемые соли с кислотами - Google Patents

Производные аминоалкилбензола или их фармацевтически приемлемые соли с кислотами Download PDF

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Publication number: RU2033991C1
Authority: RU; Russia
Prior art keywords: dimethylamino; solution; propyl; formula; compounds
Prior art date: 1989-06-08

Application number

Other languages

English (en)

Russian (ru)

Inventor

Гэри Филип

Жолидон Синэз

Цурфлю Рене

Original Assignee

Ф.Хоффманн-Ля Рош Аг

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.)

1989-06-08

Filing date

1990-05-30

Publication date

1995-04-30

1990-05-30 Application filed by Ф.Хоффманн-Ля Рош Аг filed Critical Ф.Хоффманн-Ля Рош Аг

1995-04-30 Application granted granted Critical

1995-04-30 Publication of RU2033991C1 publication Critical patent/RU2033991C1/ru

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150000003839 salts Chemical class 0.000 title claims abstract description 15
239000002253 acid Substances 0.000 title claims abstract description 13
150000007513 acids Chemical class 0.000 title claims description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 66
238000000034 method Methods 0.000 abstract description 17
239000000126 substance Substances 0.000 abstract description 13
230000015572 biosynthetic process Effects 0.000 abstract description 11
230000000694 effects Effects 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
238000001819 mass spectrum Methods 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000003921 oil Substances 0.000 description 23
235000019198 oils Nutrition 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000203 mixture Substances 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 11
229930182558 Sterol Natural products 0.000 description 11
-1 dimethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene Chemical group 0.000 description 11
150000003432 sterols Chemical class 0.000 description 11
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239000000969 carrier Substances 0.000 description 10
239000003112 inhibitor Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000012047 saturated solution Substances 0.000 description 8
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VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 7
235000011121 sodium hydroxide Nutrition 0.000 description 7
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
230000000843 anti-fungal effect Effects 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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238000012360 testing method Methods 0.000 description 6
241000222122 Candida albicans Species 0.000 description 5
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239000002585 base Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
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XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108010059597 Lanosterol synthase Proteins 0.000 description 4
102100032011 Lanosterol synthase Human genes 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
229940121375 antifungal agent Drugs 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
239000012300 argon atmosphere Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
244000053095 fungal pathogen Species 0.000 description 4
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CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000008363 phosphate buffer Substances 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
230000002195 synergetic effect Effects 0.000 description 4
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NHIRQLOJLNQLQK-UHFFFAOYSA-N 4-[7-(dimethylamino)heptyl]benzoic acid Chemical compound CN(C)CCCCCCCC1=CC=C(C(O)=O)C=C1 NHIRQLOJLNQLQK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
239000003429 antifungal agent Substances 0.000 description 3
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
229940024874 benzophenone Drugs 0.000 description 3
239000012965 benzophenone Substances 0.000 description 3
239000000872 buffer Substances 0.000 description 3
229940095731 candida albicans Drugs 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
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230000009885 systemic effect Effects 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 description 2
CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 description 2
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STPZYZSREQGDHY-NTCAYCPXSA-N (e)-3-phenyl-1-[4-(3-pyrrolidin-1-ylpropyl)phenyl]prop-2-en-1-one Chemical compound C=1C=C(CCCN2CCCC2)C=CC=1C(=O)\C=C\C1=CC=CC=C1 STPZYZSREQGDHY-NTCAYCPXSA-N 0.000 description 2
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CWQOIYVRTCRORX-UHFFFAOYSA-N 1-[4-[3-(dimethylamino)propyl]phenyl]-3-(2-methylphenyl)propan-1-one Chemical compound C1=CC(CCCN(C)C)=CC=C1C(=O)CCC1=CC=CC=C1C CWQOIYVRTCRORX-UHFFFAOYSA-N 0.000 description 2
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FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 description 2
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229920001817 Agar Polymers 0.000 description 2
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241000233866 Fungi Species 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
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KRSDSOWHQJNLFB-XFFZJAGNSA-N [4-[(z)-7-(dimethylamino)hept-1-enyl]phenyl]-phenylmethanone Chemical compound C1=CC(\C=C/CCCCCN(C)C)=CC=C1C(=O)C1=CC=CC=C1 KRSDSOWHQJNLFB-XFFZJAGNSA-N 0.000 description 2
BOEXXXCKUCRRJI-UHFFFAOYSA-N [4-[7-(dimethylamino)heptyl]phenyl]-phenylmethanone Chemical compound C1=CC(CCCCCCCN(C)C)=CC=C1C(=O)C1=CC=CC=C1 BOEXXXCKUCRRJI-UHFFFAOYSA-N 0.000 description 2
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UJZCKPGCWXGUFK-UHFFFAOYSA-N n,n-dimethyl-6-[4-(2-phenyl-1,3-dioxolan-2-yl)phenyl]hexan-1-amine Chemical compound C1=CC(CCCCCCN(C)C)=CC=C1C1(C=2C=CC=CC=2)OCCO1 UJZCKPGCWXGUFK-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Chemical class 0.000 description 1
235000008476 powdered milk Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
210000001938 protoplast Anatomy 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000941 radioactive substance Substances 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
238000009097 single-agent therapy Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000000527 sonication Methods 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
239000008117 stearic acid Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
229960002722 terbinafine Drugs 0.000 description 1
BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SU4743988 1989-06-08 1990-05-30 Производные аминоалкилбензола или их фармацевтически приемлемые соли с кислотами RU2033991C1 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH215989		1989-06-08
CH2159/89		1989-06-08

Publications (1)

Publication Number	Publication Date
RU2033991C1 true RU2033991C1 (ru)	1995-04-30

Family

ID=4227259

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU4743988 RU2033991C1 (ru)	1989-06-08	1990-05-30	Производные аминоалкилбензола или их фармацевтически приемлемые соли с кислотами

Country Status (7)

Country	Link
DD (1)	DD296911A5 (is)
HR (1)	HRP930493A2 (is)
IS (1)	IS3588A7 (is)
MX (1)	MX21001A (is)
RU (1)	RU2033991C1 (is)
UA (1)	UA18867A (is)
ZA (1)	ZA904228B (is)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2298402C2 (ru) *	2001-07-20	2007-05-10	Новартис Аг	Твердая лекарственная форма тербинафина для перорального введения

1990
- 1990-05-30 RU SU4743988 patent/RU2033991C1/ru active
- 1990-05-30 UA UA4743988A patent/UA18867A/uk unknown
- 1990-06-01 ZA ZA904228A patent/ZA904228B/xx unknown
- 1990-06-04 MX MX2100190A patent/MX21001A/es unknown
- 1990-06-05 DD DD34133490A patent/DD296911A5/de not_active IP Right Cessation
- 1990-06-07 IS IS3588A patent/IS3588A7/is unknown
1993
- 1993-03-24 HR HR930493A patent/HRP930493A2/xx not_active Application Discontinuation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Патент США 4072760, кл. A 61K 31/135, опубл. 1978. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2298402C2 (ru) *	2001-07-20	2007-05-10	Новартис Аг	Твердая лекарственная форма тербинафина для перорального введения

Also Published As

Publication number	Publication date
HRP930493A2 (en)	1996-06-30
DD296911A5 (de)	1991-12-19
IS3588A7 (is)	1990-12-09
MX21001A (es)	1993-09-01
ZA904228B (en)	1991-02-27
UA18867A (uk)	1997-12-25

Publication	Publication Date	Title
US5177067A (en)	1993-01-05	Substituted aminoalkyl biphenyl compounds and method of treating fungal infections
US4402968A (en)	1983-09-06	Antifungal benzofuranyl imidazole compounds
KR0172122B1 (ko)	1999-02-01	치환된 아미노알콕시벤젠 유도체
GB2038821A (en)	1980-07-30	N-(phenoxyalkyl)imidazoles as selective inhibitors of the thromboxane synthetase enzyme pharmaceutical compositions thereof and process for their preparation
US4282251A (en)	1981-08-04	Trans-n-cinnamyl-n-methyl-(1-naphthylmethyl)amine
US5239084A (en)	1993-08-24	Substituted aminoalkyl biphenyl compounds
US4960797A (en)	1990-10-02	N-2[(4-fluoro-phenyl)-1-methyl]-2-ethyl-N-methyl-N-propynyl amine and the method of use thereof
US5637771A (en)	1997-06-10	Compound useful for lowering cholesterol
US4146629A (en)	1979-03-27	4-arylpiperidine derivatives
RU2033991C1 (ru)	1995-04-30	Производные аминоалкилбензола или их фармацевтически приемлемые соли с кислотами
KR100195648B1 (ko)	1999-06-15	치환된 아미노알킬벤젠 유도체
US5214046A (en)	1993-05-25	Substituted aminoalkoxybenzene anti-fungicidal compositions and use
EP0346367A1 (de)	1989-12-20	Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
US4201725A (en)	1980-05-06	Secondary amines
US4820734A (en)	1989-04-11	Phenethylamine derivatives
US4304790A (en)	1981-12-08	2-(Alkylthio, alkylsulfinyl or alkylsulfonyl)-4-[2-anilinoalkylamino)-1-hydroxyethyl]phenols and derivatives thereof
KR100812843B1 (ko)	2008-03-11	3,4-디히드로이소퀴놀리늄 염 유도체
US4401831A (en)	1983-08-30	Substituted 3-aryl-2-cycloalken-1-one and method of preparation thereof
JPS58159444A (ja)	1983-09-21	２−（フエニルメチレン）シクロアルキルアミン類および−アゼチジン類
US5380755A (en)	1995-01-10	Alkyl and alkylbenzyl ethers of substituted hydroquinones
DD299176A5 (de)	1992-04-02	Substituierte aminoalkoxybenzolderivate

RU2033991C1 - Производные аминоалкилбензола или их фармацевтически приемлемые соли с кислотами - Google Patents

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Applications Claiming Priority (2)

Publications (1)

Family

ID=4227259

Family Applications (1)

Country Status (7)

Cited By (1)

Non-Patent Citations (1)

Cited By (1)

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