CA1105475A - 1,2,3,4-tetrahydro-naphthalenes - Google Patents

1,2,3,4-tetrahydro-naphthalenes

Info

Publication number: CA1105475A
Authority: CA; Canada
Prior art keywords: hydrogen; group; carbon atoms; alkyl; formula
Prior art date: 1976-12-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA292,457A

Other languages

English (en)

French (fr)

Inventor

Janos Pless

Max-Peter Seiler

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

Sandoz AG

Original Assignee

Sandoz AG

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.)

1976-12-07

Filing date

1977-12-06

Publication date

1981-07-21

1977-12-06 Application filed by Sandoz AG filed Critical Sandoz AG

1981-07-21 Application granted granted Critical

1981-07-21 Publication of CA1105475A publication Critical patent/CA1105475A/en

Status Expired legal-status Critical Current

Links

125000005329 tetralinyl group Chemical class C1(CCCC2=CC=CC=C12)* 0.000 title description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 76
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
239000001257 hydrogen Substances 0.000 claims abstract description 57
150000001875 compounds Chemical class 0.000 claims abstract description 55
125000000217 alkyl group Chemical group 0.000 claims abstract description 33
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
239000000460 chlorine Substances 0.000 claims abstract description 23
229910052801 chlorine Inorganic materials 0.000 claims abstract description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 17
125000001589 carboacyl group Chemical group 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052740 iodine Inorganic materials 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract 15
238000000034 method Methods 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
-1 methylenedioxy Chemical group 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
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 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
239000000126 substance Substances 0.000 claims 2
SXIQCXBBVCEHSI-UHFFFAOYSA-N 6-amino-6-(hydroxymethyl)-7,8-dihydro-5h-naphthalen-2-ol Chemical compound OC1=CC=C2CC(N)(CO)CCC2=C1 SXIQCXBBVCEHSI-UHFFFAOYSA-N 0.000 claims 1
208000018737 Parkinson disease Diseases 0.000 abstract description 3
230000000144 pharmacologic effect Effects 0.000 abstract description 2
208000019622 heart disease Diseases 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
239000000203 mixture Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
239000007858 starting material Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229960004756 ethanol Drugs 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000011630 iodine Chemical group 0.000 description 4
239000000725 suspension Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
206010019280 Heart failures Diseases 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
229910010084 LiAlH4 Inorganic materials 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
OVLHQUWQINALPR-UHFFFAOYSA-N azane;dichloromethane Chemical compound N.ClCCl OVLHQUWQINALPR-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
230000022244 formylation Effects 0.000 description 2
238000006170 formylation reaction Methods 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000035939 shock Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-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 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
BGWOJKDTFULIKJ-UHFFFAOYSA-N 2-azaniumyl-8-methoxy-3,4-dihydro-1h-naphthalene-2-carboxylate Chemical compound C1CC(N)(C(O)=O)CC2=C1C=CC=C2OC BGWOJKDTFULIKJ-UHFFFAOYSA-N 0.000 description 1
KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1h-naphthalen-2-one Chemical compound C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OPKSTJUWPJBCCY-UHFFFAOYSA-N 6-amino-6-(hydroxymethyl)-7,8-dihydro-5H-naphthalen-2-ol hydrobromide Chemical compound Br.NC1(CC2=CC=C(C=C2CC1)O)CO OPKSTJUWPJBCCY-UHFFFAOYSA-N 0.000 description 1
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 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
238000007045 Balz-Schiemann reaction Methods 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
101100134927 Gallus gallus COR8 gene Proteins 0.000 description 1
238000007107 Gatterman reaction Methods 0.000 description 1
QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 1
FGCVVWLDFJVVQN-UHFFFAOYSA-N N,N-bis(chlorosulfonyl)sulfamoyl chloride Chemical class ClS(=O)(=O)N(S(=O)(=O)Cl)S(=O)(=O)Cl FGCVVWLDFJVVQN-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
206010042618 Surgical procedure repeated Diseases 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001638 boron Chemical class 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
238000003682 fluorination reaction Methods 0.000 description 1
150000002221 fluorine Chemical class 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000026045 iodination Effects 0.000 description 1
238000006192 iodination reaction Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000012730 sustained-release form Substances 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

Classifications

- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (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)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA292,457A 1976-12-07 1977-12-06 1,2,3,4-tetrahydro-naphthalenes Expired CA1105475A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH1535376		1976-12-07
CH15353/76		1976-12-07
CH82/77		1977-01-05
CH8277		1977-01-05

Publications (1)

Publication Number	Publication Date
CA1105475A true CA1105475A (en)	1981-07-21

Family

ID=25683446

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA292,457A Expired CA1105475A (en)	1976-12-07	1977-12-06	1,2,3,4-tetrahydro-naphthalenes

Country Status (17)

Country	Link
JP (1)	JPS5384955A (ja)
AT (1)	AT366361B (ja)
CA (1)	CA1105475A (ja)
DE (1)	DE2752659A1 (ja)
DK (1)	DK527877A (ja)
ES (1)	ES464747A1 (ja)
FI (1)	FI773595A7 (ja)
FR (1)	FR2373513A1 (ja)
GB (1)	GB1597140A (ja)
IE (1)	IE45929B1 (ja)
IL (1)	IL53533A (ja)
NL (1)	NL7713364A (ja)
NZ (1)	NZ185884A (ja)
PH (1)	PH13932A (ja)
PT (1)	PT67365B (ja)
SE (1)	SE7713471L (ja)
SU (1)	SU927110A3 (ja)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS639500B2 (ja) *	1978-07-14	1988-02-29	Amerikan Hosupitaru Sapurai Corp
US4314082A (en) *	1978-07-14	1982-02-02	American Hospital Supply Corporation	Derivatives of 2-amino-6,7-dihydroxytetrahydro naphthalene (ADTN)
DE3062971D1 (en)	1979-09-14	1983-06-09	Sandoz Ag	Derivatives of tetraline, their preparation and medicaments containing these compounds
ATE6500T1 (de) *	1980-01-30	1984-03-15	American Hospital Supply Corporation	2-alpha-methyl-dopaminimino-6,7-dihydroxy-1,2,3 4-tetrahydronaphthalin, seine salze, und verfahren zu dessen herstellung.
SE8004002L (sv) *	1980-05-29	1981-11-30	Arvidsson Folke Lars Erik	Terapeutiskt anvendbara tetralinderivat
IL65501A (en) *	1981-05-08	1986-04-29	Astra Laekemedel Ab	1-alkyl-2-aminotetralin derivatives,process for their preparation and pharmaceutical compositions containing them
EP0091437A1 (en) *	1981-05-11	1983-10-19	Folke Lars-Erik Arvidsson	Therapeutically useful tetralin derivatives iii, processes for preparation and pharmaceutical preparations for such compounds
US4455317A (en) *	1981-06-23	1984-06-19	American Hospital Supply Corporation	Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents
US4402974A (en)	1981-06-23	1983-09-06	American Hospital Supply Corporation	Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents
US4454154A (en) *	1981-06-23	1984-06-12	American Hospital Supply Corporation	Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents
US4578403A (en) *	1981-06-23	1986-03-25	American Hospital Supply Corporation	Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents
US4559359A (en) *	1981-06-23	1985-12-17	American Hospital Supply Corporation	Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents
IT1218322B (it) *	1982-06-10	1990-04-12	Chiesi Farma Spa	Derivati di 1,2,3,4-tetraidronaftalene,procedimento di preparazione e relative composizioni farmaceutiche
US4448990A (en) *	1982-11-16	1984-05-15	Eli Lilly And Company	Hydroxyaminotetralincarboxamides
US4500545A (en) *	1982-11-16	1985-02-19	Eli Lilly And Company	Hydroxyaminotetralincarboxamides
US4657925A (en) *	1984-08-13	1987-04-14	Nelson Research & Development Co.	Method and compositions for reducing the intraocular pressure of mammals
US5177112A (en) *	1983-01-03	1993-01-05	Whitby Research, Inc.	Substituted 2-aminotetralins
US4722933A (en) *	1985-12-20	1988-02-02	Nelson Research & Development Co.	Substituted 2-aminotetralins
US4743618A (en) *	1983-01-03	1988-05-10	Nelson Research & Development Co.	Substituted 2-aminotetralins
US4564628A (en) *	1983-01-03	1986-01-14	Nelson Research & Development Co.	Substituted 2-aminotetralins
GB2157950B (en) *	1984-05-04	1988-11-02	Nelson Res & Dev	Selective d-2 dopamine receptor agonist
US5214156A (en) *	1988-03-25	1993-05-25	The Upjohn Company	Therapeutically useful tetralin derivatives
CA1331191C (en)	1988-03-25	1994-08-02	Bengt Ronny Andersson	Therapeutically useful tetralin derivatives
US5225596A (en) *	1989-01-09	1993-07-06	The Upjohn Company	Halo substituted aminotetralins
JP2931986B2 (ja) *	1989-02-17	1999-08-09	武田薬品工業株式会社	アラルキルアミン誘導体
SE8901889D0 (sv) *	1989-05-26	1989-05-26	Astra Ab	Novel 8-substituted-2-aminotetralines
EP0639557A1 (en) *	1991-03-07	1995-02-22	Zeria Pharmaceutical Co., Ltd.	Trialkylamine derivative and ameliorant for digestive tract movement containing the same
RU2185372C2 (ru) *	1996-05-31	2002-07-20	Фармация Энд Апджон Компани	Алкилзамещенные циклические амины в качестве селективных лигандов d3-допамина
IT1294931B1 (it)	1997-09-22	1999-04-23	Sigma Tau Ind Farmaceuti	Derivati della 2-amminotetralina procedimento per la loro preparazione e composizioni farmaceutiche che li contengono, attive nella
AR054363A1 (es) *	2005-05-23	2007-06-20	Astrazeneca Ab	Compuestos que exhiben actividad moduladora en el receptor 5-hidroxi-triptamina 6
EP2723727B1 (en) *	2011-06-27	2017-03-01	Shan Dong Luye Pharmaceutical Co., Ltd.	Method for industrially preparing nitrogen substituted amino-5,6,7,8-tetrahydronaphthol

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1017359A (en) *	1972-07-03	1977-09-13	Frederic P. Hauck	Substituted cyclic polymethylene phenols

1977
- 1977-11-25 DE DE19772752659 patent/DE2752659A1/de not_active Ceased
- 1977-11-28 DK DK527877A patent/DK527877A/da not_active Application Discontinuation
- 1977-11-28 FI FI773595A patent/FI773595A7/fi not_active Application Discontinuation
- 1977-11-29 SE SE7713471A patent/SE7713471L/xx not_active Application Discontinuation
- 1977-12-02 NL NL7713364A patent/NL7713364A/xx not_active Application Discontinuation
- 1977-12-05 ES ES464747A patent/ES464747A1/es not_active Expired
- 1977-12-05 IE IE2462/77A patent/IE45929B1/en unknown
- 1977-12-05 GB GB50477/77A patent/GB1597140A/en not_active Expired
- 1977-12-05 IL IL53533A patent/IL53533A/xx unknown
- 1977-12-05 PT PT67365A patent/PT67365B/pt unknown
- 1977-12-06 CA CA292,457A patent/CA1105475A/en not_active Expired
- 1977-12-06 SU SU772549950A patent/SU927110A3/ru active
- 1977-12-06 AT AT0871977A patent/AT366361B/de not_active IP Right Cessation
- 1977-12-06 JP JP14648577A patent/JPS5384955A/ja active Granted
- 1977-12-06 FR FR7736662A patent/FR2373513A1/fr active Granted
- 1977-12-06 NZ NZ185884A patent/NZ185884A/xx unknown
- 1977-12-07 PH PH20543A patent/PH13932A/en unknown

Also Published As

Publication number	Publication date
ES464747A1 (es)	1979-01-01
DE2752659A1 (de)	1978-06-08
PT67365A (fr)	1978-01-01
ATA871977A (de)	1981-08-15
PH13932A (en)	1980-11-04
JPS6214540B2 (ja)	1987-04-02
FR2373513B1 (ja)	1980-08-22
IL53533A0 (en)	1978-03-10
IL53533A (en)	1982-07-30
AT366361B (de)	1982-04-13
NL7713364A (nl)	1978-06-09
PT67365B (fr)	1979-09-20
FR2373513A1 (fr)	1978-07-07
GB1597140A (en)	1981-09-03
JPS5384955A (en)	1978-07-26
DK527877A (da)	1978-06-08
IE45929B1 (en)	1982-12-29
SE7713471L (sv)	1978-06-08
FI773595A7 (fi)	1978-06-08
SU927110A3 (ru)	1982-05-07
NZ185884A (en)	1980-04-28
IE45929L (en)	1978-06-07

Publication	Publication Date	Title
CA1105475A (en)	1981-07-21	1,2,3,4-tetrahydro-naphthalenes
HU193161B (en)	1987-08-28	Process for preparing new n-alkyl-norscopines
JP2637737B2 (ja)	1997-08-06	新規な薬剤
CA1109871A (en)	1981-09-29	Purine derivatives
CA1330560C (en)	1994-07-05	Di- and tetrahydroisoquinoline derivatives
IE45674B1 (en)	1982-10-20	Phenylethylamines
EP0028381B1 (en)	1985-04-10	Azepinoindoles, process for their production and pharmaceutical compositions containing them
EP0348223B1 (en)	1995-06-07	Novel process for the preparation of serinol
HU221625B1 (hu)	2002-12-28	Eljárás optikailag aktív 2-amino-1,2,3,4-tetrahidro-naftalin-származékok előállítására
US2759942A (en)	1956-08-21	Substituted piperidinecarboxylates and methods of preparing same
EP0138490B1 (en)	1988-04-27	4-alkyl methylenedioxy-2-1[H]-quinazolinones
JPH03120271A (ja)	1991-05-22	抗虚血活性を有するフェニルアルキルアミン誘導体
JPH01221365A (ja)	1989-09-04	化合物の新規な製造方法
GB1591723A (en)	1981-06-24	1-amino-2-hydroxy-3-heterocyclyloxy-propanes
US3200132A (en)	1965-08-10	Aminomethyl-benzofurans
CY1431A (en)	1988-09-02	3,3-dialkyl-and,3,3-alkylene-indoline derivatives,processes for their production and pharmaceutical compositions,comprising them
JPS6139305B2 (ja)	1986-09-03
US2978459A (en)	1961-04-04	Ketals of (3-indolyl)-aminoalkanones
US3988362A (en)	1976-10-26	Intermediates for preparation of 2,2,3-endotrimethyl-7-anti-amino-norbornanes
US3996383A (en)	1976-12-07	3-Alkylamino-α-aminomethyl-4-hydroxybenzyl alcohols with β-adrenergic stimulant activity
CA1271754A (en)	1990-07-17	1,5-benzoxathiepin derivatives, their production and use
JPH04210984A (ja)	1992-08-03	環生成されたイミノチアゾールの製法及び中間体
US3162637A (en)	1964-12-22	Piperazinoalkyl esters of 9-hydroxyfluorene-9-carboxylic acid
US3510516A (en)	1970-05-05	N-haloalkanoyl-2-nitrodiphenyl-amines
Blicke et al.	1954	Antispasmodics. XIV. Basic 1, 3-Dioxanes

Legal Events

Date	Code	Title	Description
1998-07-21	MKEX	Expiry