NO120686B - - Google Patents

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Publication number: NO120686B
Authority: NO; Norway
Prior art keywords: ethanol; compound; ether; hydrogen; butylamino
Prior art date: 1966-10-19

Application number

NO170180A

Other languages

English (en)

Norwegian (no)

Inventor

K Wetterlin

Original Assignee

Draco Ab

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.)

1966-10-19

Filing date

1967-10-18

Publication date

1970-11-23

1967-10-18 Application filed by Draco Ab filed Critical Draco Ab

1970-04-07 Priority to NO128170A priority Critical patent/NO124723B/no

1970-08-05 Priority to NO302670A priority patent/NO132866C/no

1970-11-23 Publication of NO120686B publication Critical patent/NO120686B/no

Links

150000001875 compounds Chemical class 0.000 claims description 44
-1 dicarbonyl compound Chemical class 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
238000003776 cleavage reaction Methods 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
150000002118 epoxides Chemical class 0.000 claims description 2
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 27
230000000694 effects Effects 0.000 description 25
238000002844 melting Methods 0.000 description 25
230000008018 melting Effects 0.000 description 25
238000002360 preparation method Methods 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000047 product Substances 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 13
239000012071 phase Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000003054 catalyst Substances 0.000 description 12
238000010992 reflux Methods 0.000 description 12
238000001704 evaporation Methods 0.000 description 11
239000012362 glacial acetic acid Substances 0.000 description 11
230000008020 evaporation Effects 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
238000000034 method Methods 0.000 description 7
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
229940124630 bronchodilator Drugs 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
KOJXGMJOTRYLBD-UHFFFAOYSA-N 1-[3,5-bis(phenylmethoxy)phenyl]ethanone Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)C)=CC=1OCC1=CC=CC=C1 KOJXGMJOTRYLBD-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
230000000572 bronchospasmolytic effect Effects 0.000 description 5
239000013078 crystal Substances 0.000 description 5
229910000042 hydrogen bromide Inorganic materials 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
230000000747 cardiac effect Effects 0.000 description 4
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
GWIBCCZNAYLLCD-UHFFFAOYSA-N 3,5-bis(phenylmethoxy)benzoyl chloride Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)Cl)=CC=1OCC1=CC=CC=C1 GWIBCCZNAYLLCD-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
102100040999 Catechol O-methyltransferase Human genes 0.000 description 3
108020002739 Catechol O-methyltransferase Proteins 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000007883 bronchodilation Effects 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 3
229960001317 isoprenaline Drugs 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
210000003205 muscle Anatomy 0.000 description 3
210000004165 myocardium Anatomy 0.000 description 3
DLSOILHAKCBARI-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NCC1=CC=CC=C1 DLSOILHAKCBARI-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
230000004936 stimulating effect Effects 0.000 description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
210000003437 trachea Anatomy 0.000 description 3
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
229910021590 Copper(II) bromide Inorganic materials 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 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
IGHOBBJYMZCUCE-UHFFFAOYSA-N [3-acetyloxy-5-[2-(tert-butylamino)-1-hydroxyethyl]phenyl] acetate Chemical compound CC(=O)OC1=CC(OC(C)=O)=CC(C(O)CNC(C)(C)C)=C1 IGHOBBJYMZCUCE-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000010009 beating Methods 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
OEZNULIHEQCKJR-UHFFFAOYSA-N ethanol;hydrobromide Chemical compound Br.CCO OEZNULIHEQCKJR-UHFFFAOYSA-N 0.000 description 2
APHYVLPIZUVDTK-UHFFFAOYSA-N ethyl 3,5-dihydroxybenzoate Chemical compound CCOC(=O)C1=CC(O)=CC(O)=C1 APHYVLPIZUVDTK-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
230000005923 long-lasting effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229960002748 norepinephrine Drugs 0.000 description 2
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 1
QFBOZEACKUKEBR-UHFFFAOYSA-N 1-[3,5-bis(phenylmethoxy)phenyl]-2-(tert-butylamino)ethanol Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(O)CNC(C)(C)C)=CC=1OCC1=CC=CC=C1 QFBOZEACKUKEBR-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
GYEYPHBTKAEWHH-UHFFFAOYSA-N 2,3-bis(phenylmethoxy)benzoic acid Chemical compound C=1C=CC=CC=1COC=1C(C(=O)O)=CC=CC=1OCC1=CC=CC=C1 GYEYPHBTKAEWHH-UHFFFAOYSA-N 0.000 description 1
ZIJJNHMJIHJFSI-UHFFFAOYSA-N 2-[3,5-bis(phenylmethoxy)phenyl]-2-oxoacetaldehyde Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)C=O)=CC=1OCC1=CC=CC=C1 ZIJJNHMJIHJFSI-UHFFFAOYSA-N 0.000 description 1
LCQWVIZYGHCUGF-UHFFFAOYSA-N 2-[benzyl(tert-butyl)amino]-1-[3,5-bis(phenylmethoxy)phenyl]ethanol Chemical compound C=1C=CC=CC=1CN(C(C)(C)C)CC(O)C(C=C(OCC=1C=CC=CC=1)C=1)=CC=1OCC1=CC=CC=C1 LCQWVIZYGHCUGF-UHFFFAOYSA-N 0.000 description 1
YUDPEQPLTRKPHY-UHFFFAOYSA-N 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol;hydrobromide Chemical compound Br.CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 YUDPEQPLTRKPHY-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-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
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
WKHOPHIMYDJVSA-UHFFFAOYSA-N [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC(OC(=O)C(C)C)=CC(C(O)CNC(C)(C)C)=C1 WKHOPHIMYDJVSA-UHFFFAOYSA-N 0.000 description 1
BWZYYMJUBTWGSP-UHFFFAOYSA-N [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate;hydrobromide Chemical compound Br.CC(C)C(=O)OC1=CC(OC(=O)C(C)C)=CC(C(O)CNC(C)(C)C)=C1 BWZYYMJUBTWGSP-UHFFFAOYSA-N 0.000 description 1
MQYRDZBXGQXLSR-UHFFFAOYSA-N [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-propanoyloxyphenyl] propanoate Chemical compound CCC(=O)OC1=CC(OC(=O)CC)=CC(C(O)CNC(C)(C)C)=C1 MQYRDZBXGQXLSR-UHFFFAOYSA-N 0.000 description 1
SODGANCLSCQOSS-UHFFFAOYSA-N [3-acetyloxy-5-[2-(tert-butylamino)-1-hydroxyethyl]phenyl] acetate;hydrobromide Chemical compound Br.CC(=O)OC1=CC(OC(C)=O)=CC(C(O)CNC(C)(C)C)=C1 SODGANCLSCQOSS-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000004927 clay Substances 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
RQXAEHUFPQJLDD-UHFFFAOYSA-N ethyl 3,5-bis(phenylmethoxy)benzoate Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)OCC)=CC=1OCC1=CC=CC=C1 RQXAEHUFPQJLDD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000003517 fume Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
210000004185 liver Anatomy 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
150000004682 monohydrates Chemical class 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
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
CQKAPARXKPTKBK-UHFFFAOYSA-N tert-butylazanium;bromide Chemical compound Br.CC(C)(C)N CQKAPARXKPTKBK-UHFFFAOYSA-N 0.000 description 1
239000012085 test solution Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO170180A 1966-10-19 1967-10-18 NO120686B (es)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
NO128170A NO124723B (es)	1967-10-18	1970-04-07
NO302670A NO132866C (es)	1966-10-19	1970-08-05

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE14182/66A SE335359B (es)	1966-10-19	1966-10-19

Publications (1)

Publication Number	Publication Date
NO120686B true NO120686B (es)	1970-11-23

Family

ID=20298669

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO170180A NO120686B (es)	1966-10-19	1967-10-18

Country Status (13)

Country	Link
AT (4)	AT287679B (es)
BE (1)	BE704932A (es)
CH (1)	CH510625A (es)
DE (2)	DE1793759C3 (es)
DK (2)	DK128491B (es)
ES (5)	ES346131A1 (es)
FI (1)	FI50786C (es)
FR (1)	FR8011M (es)
GB (1)	GB1199630A (es)
IT (1)	IT8048168A0 (es)
NL (2)	NL151693B (es)
NO (1)	NO120686B (es)
SE (1)	SE335359B (es)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4419364A (en)	1980-07-09	1983-12-06	Aktiebolaget Draco	Bronchospasmolytic carbamate derivatives

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4138581A (en)	1969-04-01	1979-02-06	Sterling Drugs Inc.	3(Hydroxy or hydroxymethyl)-4(hydroxy)-α-(aminomethyl)benzyl alcohols
DE3163114D1 (en) *	1980-07-09	1984-05-17	Draco Ab	Therapeutically active derivatives of phenylethanol amines
US4853381A (en) *	1984-04-17	1989-08-01	Glaxo Group Limited	Ethanolamine compounds
US4581225A (en) *	1984-04-25	1986-04-08	Eli Lilly And Company	Sustained release intranasal formulation and method of use thereof
EP0213108A3 (de) *	1985-06-26	1987-07-15	Kurt Dr. Burghart	Pharmazeutische Zubereitung mit einem Antihypotonikum als wirksames Mittel
WO2013081565A1 (en)	2011-11-21	2013-06-06	Mahmut Bilgic	Pharmaceutical compositions comprising roflumilast and terbutaline
US9784726B2 (en)	2013-01-08	2017-10-10	Atrogi Ab	Screening method, a kit, a method of treatment and a compound for use in a method of treatment
EP3600275A1 (en)	2017-03-27	2020-02-05	Ilko Ilaç Sanayi Ve Ticaret Anonim Sirketi	Stabilized pharmaceutical syrup composition comprising terbutaline sulphate and ambroxol hydrochloride
GB201714736D0 (en)	2017-09-13	2017-10-25	Atrogi Ab	New compounds and uses
GB201714740D0 (en)	2017-09-13	2017-10-25	Atrogi Ab	New compounds and uses
GB201714745D0 (en)	2017-09-13	2017-10-25	Atrogi Ab	New compounds and uses
GB201714734D0 (en)	2017-09-13	2017-10-25	Atrogi Ab	New compounds and uses
CN110057932B (zh) *	2019-04-22	2022-03-15	上海旭东海普药业有限公司	高效液相色谱分析硫酸特布他林有关物质的方法
CN111440078A (zh) *	2020-04-26	2020-07-24	梯尔希（南京）药物研发有限公司	特布他林衍生物的制备方法
CN113264839B (zh) *	2021-04-27	2022-08-30	苏州弘森药业股份有限公司	一种使用手性辅基制备左旋特布他林的方法
GB202205895D0 (en)	2022-04-22	2022-06-08	Atrogi Ab	New medical uses
WO2024153813A1 (en)	2023-01-20	2024-07-25	Atrogi Ab	Beta 2-adrenergic receptor agonists for treatment or prevention of muscle wasting

1966
- 1966-10-19 SE SE14182/66A patent/SE335359B/xx unknown
1967
- 1967-10-10 AT AT09421/69A patent/AT287679B/de active
- 1967-10-10 AT AT941969A patent/AT288356B/de not_active IP Right Cessation
- 1967-10-10 AT AT09420/69A patent/AT287678B/de active
- 1967-10-10 AT AT915967A patent/AT286964B/de not_active IP Right Cessation
- 1967-10-11 BE BE704932D patent/BE704932A/xx not_active IP Right Cessation
- 1967-10-12 CH CH1425567A patent/CH510625A/de not_active IP Right Cessation
- 1967-10-16 ES ES346131A patent/ES346131A1/es not_active Expired
- 1967-10-17 DE DE1793759A patent/DE1793759C3/de not_active Expired
- 1967-10-17 DE DE1643296A patent/DE1643296C3/de not_active Expired
- 1967-10-17 FR FR124741A patent/FR8011M/fr not_active Expired
- 1967-10-18 DK DK518567AA patent/DK128491B/da unknown
- 1967-10-18 NO NO170180A patent/NO120686B/no unknown
- 1967-10-18 GB GB47505/67A patent/GB1199630A/en not_active Expired
- 1967-10-19 NL NL676714191A patent/NL151693B/xx not_active IP Right Cessation
- 1967-10-19 FI FI672811A patent/FI50786C/fi active
1968
- 1968-12-14 ES ES361433A patent/ES361433A1/es not_active Expired
- 1968-12-14 ES ES361431A patent/ES361431A1/es not_active Expired
- 1968-12-14 ES ES361429A patent/ES361429A1/es not_active Expired
- 1968-12-14 ES ES361432A patent/ES361432A1/es not_active Expired
1975
- 1975-11-27 NL NL7513854A patent/NL7513854A/xx unknown
1976
- 1976-10-18 DK DK468876A patent/DK468876A/da unknown
1980
- 1980-03-14 IT IT8048168A patent/IT8048168A0/it unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4419364A (en)	1980-07-09	1983-12-06	Aktiebolaget Draco	Bronchospasmolytic carbamate derivatives

Also Published As

Publication number	Publication date
DE1643296A1 (de)	1971-09-30
NL151693B (nl)	1976-12-15
DK128491B (da)	1974-05-13
AT287679B (de)	1971-02-10
AT286964B (de)	1971-01-11
FI50786B (es)	1976-03-31
DK468876A (da)	1976-10-18
ES361433A1 (es)	1970-11-01
FR8011M (es)	1970-07-27
SE335359B (es)	1971-05-24
GB1199630A (en)	1970-07-22
DE1793759A1 (de)	1973-08-16
ES361429A1 (es)	1970-11-01
AT287678B (de)	1971-02-10
NL6714191A (es)	1968-04-22
DE1793759B2 (de)	1978-05-11
DE1643296C3 (de)	1974-06-12
ES361432A1 (es)	1970-11-01
ES361431A1 (es)	1970-11-01
DE1643296B2 (de)	1973-10-25
IT8048168A0 (it)	1980-03-14
CH510625A (de)	1971-07-31
FI50786C (fi)	1976-07-12
AT288356B (de)	1971-03-10
ES346131A1 (es)	1969-05-16
DE1793759C3 (de)	1979-01-11
BE704932A (es)	1968-02-15
NL7513854A (nl)	1976-03-31

Publication	Publication Date	Title
NO120686B (es)	1970-11-23
KR880002310B1 (ko)	1988-10-22	펜에탄올 아민류의 제조방법
JPH02231486A (ja)	1990-09-13	新規β―アドレナリン作動剤
NO135140B (es)	1976-11-08
NO166164B (no)	1991-03-04	Festeanordning til aa etablere elektrisk forbindelse med en engangs hudelektrode.
EP0147475A1 (en)	1985-07-10	Aminocyclohexanol derivatives having an expectorant activity, process for their preparation and pharmaceutical compositions containing them
JPS6341910B2 (es)	1988-08-19
US4855422A (en)	1989-08-08	Process for the preparation of azoniaspironortropanol esters
NO140378B (no)	1979-05-14	Fremgangsmaate for fremstilling av 1-(3,5-dihydroksyfenyl)-1-hydroksy-2-(1-methyl-2-(4-hydroksyfenyl)-etyl)-aminoetan
US4614806A (en)	1986-09-30	Process for the asymmetric synthesis of chiral indoline-2-carboxylic acids
US4822895A (en)	1989-04-18	3-aminoazetidine, its salts and intermediates of synthesis
US3065265A (en)	1962-11-20	Amino acid hydrazides
US4283410A (en)	1981-08-11	3-Amino or amido-2-(1H-indol-3-yl) propanoic acid derivatives
JPS61500615A (ja)	1986-04-03	化学合成
BOSE et al.	1959	Some Derivatives of Glycineamidine1
US3775479A (en)	1973-11-27	Amine compounds
NO132866B (es)	1975-10-13
US4304930A (en)	1981-12-08	Process for the preparation of 2-(3-phenoxy-phenyl)-propionic acid
FR652M (fr)	1961-06-19	Nouveau médicament, contenant comme composé actif un dérivé de l’indole ou un de ses sels.
GB2023590A (en)	1980-01-03	3-amino-2-(5-fluoro and 5- methoxy-1H-indol-3-yl) Propanoic Acid Derivatives and Their Preparation and Use
NO126437B (es)	1973-02-05
EP0489548B1 (en)	1994-12-14	A process for the preparation of 2(R)-methyl-4,4,4-trifluorobutylamine, intermediates, and a process for the preparation of a derivative thereof
US2970159A (en)	1961-01-31	Hydrazine derivatives
US3947584A (en)	1976-03-30	Novel indolyl alkyl amines, method of producing same, and their use as anorectic agents
US4283336A (en)	1981-08-11	Process for the preparation of 3-amino-2-(5-fluoro and 5-methoxy-1H-indol-3-yl)propanoic acid derivatives

NO120686B - - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (2)

Applications Claiming Priority (1)

Publications (1)

Family

ID=20298669

Family Applications (1)

Country Status (13)

Cited By (1)

Families Citing this family (17)

Cited By (1)

Also Published As

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