DD297401A5 - 2-amino-7-carbamoyl-1,2,3,4-tetrahydronapthaline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel - Google Patents

2-amino-7-carbamoyl-1,2,3,4-tetrahydronapthaline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel Download PDF

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Publication number: DD297401A5
Authority: DD; German Democratic Republic
Prior art keywords: amino; tetrahydronaphthalene; alkyl; general formula; hydrogen
Prior art date: 1989-07-22

Application number

DD90342912A

Other languages

German (de)

English (en)

Inventor

Matthias Grauert

Herbert Merz

Joachim Mierau

Guenter Schingnitz

Original Assignee

��@��@��k��

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.)

1989-07-22

Filing date

1990-07-19

Publication date

1992-01-09

1990-07-19 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1992-01-09 Publication of DD297401A5 publication Critical patent/DD297401A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 39
239000003814 drug Substances 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title description 9
238000002360 preparation method Methods 0.000 claims abstract description 25
230000008569 process Effects 0.000 claims abstract description 10
-1 C 1 -C 6 -alkyl Chemical group 0.000 claims description 57
239000000203 mixture Substances 0.000 claims description 38
239000002253 acid Substances 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
DLDAYSOYQANWCO-UHFFFAOYSA-N 7-amino-5,6,7,8-tetrahydronaphthalene-2-carboxamide Chemical class C1=C(C(N)=O)C=C2CC(N)CCC2=C1 DLDAYSOYQANWCO-UHFFFAOYSA-N 0.000 claims description 13
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
239000000543 intermediate Substances 0.000 claims description 5
KCRSKKOKQGALFB-UHFFFAOYSA-N 7-amino-5,6,7,8-tetrahydronaphthalene-2-carbonitrile Chemical class C1=C(C#N)C=C2CC(N)CCC2=C1 KCRSKKOKQGALFB-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 2
230000003291 dopaminomimetic effect Effects 0.000 claims description 2
125000004970 halomethyl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
238000006243 chemical reaction Methods 0.000 description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
235000019441 ethanol Nutrition 0.000 description 19
239000004480 active ingredient Substances 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
125000006239 protecting group Chemical group 0.000 description 16
239000002585 base Substances 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 15
239000000126 substance Substances 0.000 description 15
150000007513 acids Chemical class 0.000 description 14
FISUQAVKGARTJH-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-2,7-diamine Chemical class C1=C(N)C=C2CC(N)CCC2=C1 FISUQAVKGARTJH-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000013543 active substance Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
150000003512 tertiary amines Chemical class 0.000 description 10
PLRACCBDVIHHLZ-UHFFFAOYSA-N 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1N(C)CCC(C=2C=CC=CC=2)=C1 PLRACCBDVIHHLZ-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
DPQAXNSOFFYKDS-UHFFFAOYSA-N Talipexole dihydrochloride Chemical compound Cl.Cl.C1CN(CC=C)CCC2=C1N=C(N)S2 DPQAXNSOFFYKDS-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229930195733 hydrocarbon Natural products 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
238000007792 addition Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000013078 crystal Substances 0.000 description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
239000002274 desiccant Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
150000004820 halides Chemical class 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 7
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
239000000284 extract Substances 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
239000002674 ointment Substances 0.000 description 6
239000000546 pharmaceutical excipient Substances 0.000 description 6
238000006268 reductive amination reaction Methods 0.000 description 6
239000000829 suppository Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
IPHFEAMSIOVYCA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene;hydrochloride Chemical compound Cl.C1=CC=C2CCCCC2=C1 IPHFEAMSIOVYCA-UHFFFAOYSA-N 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
230000029936 alkylation Effects 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
230000037396 body weight Effects 0.000 description 5
150000001728 carbonyl compounds Chemical class 0.000 description 5
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
229960003638 dopamine Drugs 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
150000004678 hydrides Chemical class 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
230000001242 postsynaptic effect Effects 0.000 description 5
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 5
238000007127 saponification reaction Methods 0.000 description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
230000008859 change Effects 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000008298 dragée Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
229940098779 methanesulfonic acid Drugs 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
239000006187 pill Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
239000011877 solvent mixture Substances 0.000 description 4
150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
125000005490 tosylate group Chemical group 0.000 description 4
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
241000282693 Cercopithecidae Species 0.000 description 3
238000007445 Chromatographic isolation Methods 0.000 description 3
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
238000009835 boiling Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
239000006071 cream Substances 0.000 description 3
MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229960004502 levodopa Drugs 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
230000003518 presynaptic effect Effects 0.000 description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
NCNSBFDGXBKAKB-UHFFFAOYSA-N (methylsulfanyl)acetaldehyde Chemical compound CSCC=O NCNSBFDGXBKAKB-UHFFFAOYSA-N 0.000 description 2
VDLWTJCSPSUGOA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)CCCC2=C1 VDLWTJCSPSUGOA-UHFFFAOYSA-N 0.000 description 2
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
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 2
IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
SMEYBMVDKZIHLQ-UHFFFAOYSA-N 7-(dipropylamino)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile Chemical compound C1=C(C#N)C=C2CC(N(CCC)CCC)CCC2=C1 SMEYBMVDKZIHLQ-UHFFFAOYSA-N 0.000 description 2
UVLFQPWEKCUJLT-UHFFFAOYSA-N 7-(dipropylamino)-n-methyl-5,6,7,8-tetrahydronaphthalene-2-carboxamide;hydrochloride Chemical compound Cl.C1=C(C(=O)NC)C=C2CC(N(CCC)CCC)CCC2=C1 UVLFQPWEKCUJLT-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
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239000008101 lactose Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
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150000002826 nitrites Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
IJNJLGFTSIAHEA-UHFFFAOYSA-N prop-2-ynal Chemical compound O=CC#C IJNJLGFTSIAHEA-UHFFFAOYSA-N 0.000 description 1
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125000004673 propylcarbonyl group Chemical group 0.000 description 1
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238000000746 purification Methods 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
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239000008117 stearic acid Substances 0.000 description 1
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150000003460 sulfonic acids Chemical class 0.000 description 1
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239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
LCZVKKUAUWQDPX-UHFFFAOYSA-N tert-butyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl]amino]acetate Chemical compound CC(=O)OC1=CC=CC=C1CN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC1=CC=CC=C1OC(C)=O LCZVKKUAUWQDPX-UHFFFAOYSA-N 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- A61P9/06—Antiarrhythmics
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/48—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system of the same carbon skeleton
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD90342912A 1989-07-22 1990-07-19 2-amino-7-carbamoyl-1,2,3,4-tetrahydronapthaline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel DD297401A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3924365A DE3924365A1 (de)	1989-07-22	1989-07-22	2-amino-7-carbamoyl-1,2,3,4- tetrahydronaphthaline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
DD297401A5 true DD297401A5 (de)	1992-01-09

Family

ID=6385664

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90342912A DD297401A5 (de)	1989-07-22	1990-07-19	2-amino-7-carbamoyl-1,2,3,4-tetrahydronapthaline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel

Country Status (13)

Country	Link
EP (1)	EP0435988A1 (ja)
JP (1)	JPH04500815A (ja)
KR (1)	KR920701133A (ja)
AU (1)	AU630725B2 (ja)
CA (1)	CA2033323A1 (ja)
DD (1)	DD297401A5 (ja)
DE (1)	DE3924365A1 (ja)
IE (1)	IE902655A1 (ja)
IL (1)	IL95142A0 (ja)
NZ (1)	NZ234590A (ja)
PT (1)	PT94780A (ja)
WO (1)	WO1991001297A1 (ja)
ZA (1)	ZA905715B (ja)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100195656B1 (ko) *	1989-05-31	1999-06-15	로버트 에이.아미테이지	치료학적으로 유용한 2-아미노테트랄린 유도체
EP0499755A1 (fr) *	1991-02-18	1992-08-26	MIDY S.p.A.	Nouvelles phényléthanolaminotétralines, procédé pour leur préparation, intermédiaires dans ce procédé et compositions pharmaceutiques les contenant
DK148292D0 (da) *	1992-12-09	1992-12-09	Lundbeck & Co As H	Forbindelser
NZ569608A (en) *	2006-01-06	2011-09-30	Sepracor Inc	Tetralone-based monoamine reuptake inhibitors

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4448990A (en) *	1982-11-16	1984-05-15	Eli Lilly And Company	Hydroxyaminotetralincarboxamides
DE3719924A1 (de) *	1986-12-22	1988-06-30	Bayer Ag	8-substituierte 2-aminotetraline
KR100195656B1 (ko) *	1989-05-31	1999-06-15	로버트 에이.아미테이지	치료학적으로 유용한 2-아미노테트랄린 유도체

1989
- 1989-07-22 DE DE3924365A patent/DE3924365A1/de not_active Withdrawn
1990
- 1990-07-18 EP EP90910685A patent/EP0435988A1/de not_active Withdrawn
- 1990-07-18 AU AU59586/90A patent/AU630725B2/en not_active Ceased
- 1990-07-18 KR KR1019910700299A patent/KR920701133A/ko not_active Withdrawn
- 1990-07-18 JP JP2509979A patent/JPH04500815A/ja active Pending
- 1990-07-18 CA CA002033323A patent/CA2033323A1/en not_active Abandoned
- 1990-07-18 WO PCT/EP1990/001174 patent/WO1991001297A1/de not_active Ceased
- 1990-07-19 DD DD90342912A patent/DD297401A5/de not_active IP Right Cessation
- 1990-07-20 ZA ZA905715A patent/ZA905715B/xx unknown
- 1990-07-20 NZ NZ234590A patent/NZ234590A/en unknown
- 1990-07-20 IE IE265590A patent/IE902655A1/en unknown
- 1990-07-20 PT PT94780A patent/PT94780A/pt not_active Application Discontinuation
- 1990-07-20 IL IL95142A patent/IL95142A0/xx unknown

Also Published As

Publication number	Publication date
ZA905715B (en)	1992-03-25
IE902655A1 (en)	1991-02-27
IL95142A0 (en)	1991-06-10
WO1991001297A1 (de)	1991-02-07
DE3924365A1 (de)	1991-01-24
EP0435988A1 (de)	1991-07-10
AU5958690A (en)	1991-02-22
JPH04500815A (ja)	1992-02-13
KR920701133A (ko)	1992-08-11
NZ234590A (en)	1992-07-28
AU630725B2 (en)	1992-11-05
CA2033323A1 (en)	1991-01-23
PT94780A (pt)	1991-03-20

Legal Events

Date	Code	Title	Description
2000-03-30	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
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