CH380746A - Verfahren zur Herstellung neuer sekundärer Amine - Google Patents

Verfahren zur Herstellung neuer sekundärer Amine

Info

Publication number: CH380746A
Authority: CH; Switzerland
Prior art keywords: mol; ethyl; formula; phenoxy; bromide
Prior art date: 1958-11-06

Application number

CH6587558A

Other languages

German (de)

English (en)

Inventor

Jean Dr Druey

Karl Dr Schenker

Original Assignee

Ciba Geigy

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.)

1958-11-06

Filing date

1958-11-06

Publication date

1964-08-15

Priority to NL245051A priority Critical patent/NL133044C/xx

1958-11-06 Application filed by Ciba Geigy filed Critical Ciba Geigy

1958-11-06 Priority to CH6587558A priority patent/CH380746A/de

1959-09-23 Priority to US841688A priority patent/US3105854A/en

1959-10-27 Priority to DEC20049A priority patent/DE1161286B/de

1959-11-02 Priority to FR809040A priority patent/FR1278618A/fr

1959-11-05 Priority to BE584358A priority patent/BE584358A/fr

1960-08-10 Priority to FR835450A priority patent/FR302M/fr

1960-08-10 Priority to FR835449A priority patent/FR163M/fr

1964-08-15 Publication of CH380746A publication Critical patent/CH380746A/de

Links

238000000034 method Methods 0.000 title claims description 19
238000002360 preparation method Methods 0.000 title claims description 5
150000003335 secondary amines Chemical class 0.000 title claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
239000004215 Carbon black (E152) Substances 0.000 claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
230000001419 dependent effect Effects 0.000 claims 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
-1 hydrocarbon radical Chemical class 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 11
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 11
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Natural products OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000011734 sodium Substances 0.000 description 9
239000013078 crystal Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000000155 melt Substances 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 5
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000007788 liquid Substances 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000001816 cooling Methods 0.000 description 3
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
WTFGCLZKNHMTOD-UHFFFAOYSA-N 3-(2-methylpropoxy)phenol Chemical compound CC(C)COC1=CC=CC(O)=C1 WTFGCLZKNHMTOD-UHFFFAOYSA-N 0.000 description 2
IOOCVIRRKFNHEL-UHFFFAOYSA-N 3-pentoxyphenol Chemical compound CCCCCOC1=CC=CC(O)=C1 IOOCVIRRKFNHEL-UHFFFAOYSA-N 0.000 description 2
YYMPIPSWQOGUME-UHFFFAOYSA-N 3-propoxyphenol Chemical compound CCCOC1=CC=CC(O)=C1 YYMPIPSWQOGUME-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
229940100684 pentylamine Drugs 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical group [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 description 1
VGIJZDWQVCXVNL-UHFFFAOYSA-N 3-butoxyphenol Chemical compound CCCCOC1=CC=CC(O)=C1 VGIJZDWQVCXVNL-UHFFFAOYSA-N 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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
BFKVXNPJXXJUGQ-UHFFFAOYSA-N [CH2]CCCC Chemical compound [CH2]CCCC BFKVXNPJXXJUGQ-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
238000001035 drying Methods 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940095574 propionic acid Drugs 0.000 description 1
235000019260 propionic acid Nutrition 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
239000011541 reaction mixture Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH6587558A 1958-11-06 1958-11-06 Verfahren zur Herstellung neuer sekundärer Amine CH380746A (de)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
NL245051A NL133044C (fr)	1958-11-06
CH6587558A CH380746A (de)	1958-11-06	1958-11-06	Verfahren zur Herstellung neuer sekundärer Amine
US841688A US3105854A (en)	1958-11-06	1959-09-23	Meta-substituted phenoxyethylamines
DEC20049A DE1161286B (de)	1958-11-06	1959-10-27	Verfahren zur Herstellung neuer Amine
FR809040A FR1278618A (fr)	1958-11-06	1959-11-02	Procédé de préparation de nouvelles phénoxy-alcoyl-amines
BE584358A BE584358A (fr)	1958-11-06	1959-11-05	Procédé de préparation de nouvelles phénoxy-alcoyl-amines
FR835450A FR302M (fr)	1958-11-06	1960-08-10	Nouvelle m-butoxy-phénoxy-éthylamine utilisable en thérapeutique.
FR835449A FR163M (fr)	1958-11-06	1960-08-10	Nouvelle phénoxy-éthylamine utilisable en thérapeutique.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6587558A CH380746A (de)	1958-11-06	1958-11-06	Verfahren zur Herstellung neuer sekundärer Amine

Publications (1)

Publication Number	Publication Date
CH380746A true CH380746A (de)	1964-08-15

Family

ID=4526704

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6587558A CH380746A (de)	1958-11-06	1958-11-06	Verfahren zur Herstellung neuer sekundärer Amine

Country Status (3)

Country	Link
US (1)	US3105854A (fr)
CH (1)	CH380746A (fr)
FR (1)	FR302M (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1220440B (de) *	1962-02-14	1966-07-07	Sanol Arznei Schwarz Gmbh	Verfahren zur Herstellung von Derivaten des 1-(o-Bromphenoxy)-2-hydroxy-3-amino-propans und deren Saeureadditionssalzen
US3205136A (en) *	1962-12-24	1965-09-07	Smith Kline French Lab	Antidepressant phenyloxyalkylamines
US3988475A (en) *	1974-02-05	1976-10-26	Istituto Luso Farmaco D'italia S.R.L.	Phenoxyalkylamines
AR004691A1 (es) *	1995-10-27	1999-03-10	Astrazeneca Ab	Nuevos derivados de [3-alcoxi-fenoxi-)-etil]-dialquilamina, una composicion farmaceutica que los comprende, su uso como anestesicos locales y unprocedimiento para su preparacion
US7799337B2 (en)	1997-07-21	2010-09-21	Levin Bruce H	Method for directed intranasal administration of a composition
US6432986B2 (en)	1997-07-21	2002-08-13	Bruce H. Levin	Compositions, kits, and methods for inhibiting cerebral neurovascular disorders and muscular headaches
SE9704770D0 (sv) *	1997-12-19	1997-12-19	Astra Ab	New use
SE9704835D0 (sv)	1997-12-22	1997-12-22	Astra Ab	New compound
WO2009045479A1 (fr)	2007-10-05	2009-04-09	Acucela Inc.	Composés d'alcoxy pour le traitement de maladies
EP4000610A1 (fr)	2009-07-02	2022-05-25	Acucela Inc.	Pharmacologie de modulateurs de cycle visuel

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB300695A (en) *	1927-08-18	1928-11-19	Ig Farbenindustrie Ag	Process for the manufacture of basic ethers of resorcinol
US2765338A (en) *	1952-06-08	1956-10-02	Cilag Ltd	New aliphatic acid amide derivatives and processes for the production thereof
US2967201A (en) *	1958-06-02	1961-01-03	Lilly Co Eli	Alkylaminoalkyl ethers of phenols

1958
- 1958-11-06 CH CH6587558A patent/CH380746A/de unknown
1959
- 1959-09-23 US US841688A patent/US3105854A/en not_active Expired - Lifetime
1960
- 1960-08-10 FR FR835450A patent/FR302M/fr not_active Expired

Also Published As

Publication number	Publication date
US3105854A (en)	1963-10-01
FR302M (fr)	1961-03-20

Publication	Publication Date	Title
DD141520A5 (de)	1980-05-07	Verfahren zur herstellung neuer derivate von 4-amino-5-alkylsulfonyl-ortho-anisamiden
DE2508045C2 (de)	1986-11-06	Substituierte n-(1-benzylpyrrolidinyl-2-alkyl)-benzamide, verfahren zu deren herstellung und diese enthaltende arzneimittel
DE3026201A1 (de)	1981-02-26	Aminoaetheroxide, verfahren zu ihrer herstellung sowie ihre therapeutische verwendung
CH380746A (de)	1964-08-15	Verfahren zur Herstellung neuer sekundärer Amine
DE2431192C2 (de)	1982-12-09	O,O-DiäthylS-[6-chlor-1,3-benzoxazolon-3-yl-methyl]-dithiophosphat
DE2934746A1 (de)	1981-03-19	Oxoimidazolinalkansaeuren, deren salze und ester sowie verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE2427272C3 (de)	1981-10-01	1-(2-(β-Naphthyloxy)-äthyl)-3-methyl -pyrazolon-(5), Verfahren sowie Verwendung als Antithrombotikum
DE1668550C (fr)	1973-01-18
DE568675C (de)	1933-01-27	Verfahren zur Herstellung von O-Alkyl-, Oxyalkyl- oder Alkylaminoalkylaethern des Harmols oder Harmalols
DE2123555B2 (de)	1978-05-03	Verfahren zur Herstellung von 21-Desoxy-21-N-(N'-methyIpiperazinyl)-prednisolon und dessen Salzen
DE1670143C3 (fr)	1974-05-30
DE2065698B2 (de)	1979-01-04	Verfahren zur Herstellung von 2-Isopropyl-6-methyl-4(3H)-pyrimidon
DE886744C (de)	1953-08-17	Verfahren zur Herstellung von Dicarbonsaeure-bis-cholinestern, ihren Salzen und niederen Homologen
DE1166782B (de)	1964-04-02	Verfahren zur Herstellung von substituierten aromatischen Dicarbonsaeureimiden und deren Salzen
AT234691B (de)	1964-07-10	Verfahren zur Herstellung von neuen Piperidinderivaten
AT221505B (de)	1962-06-12	Verfahren zur Herstellung neuer basischer Phenoläther und ihrer Salze
AT204046B (de)	1959-06-25	Verfahren zur Herstellung von neuen Piperazinderivaten und von deren Salzen
AT226732B (de)	1963-04-10	Verfahren zur Herstellung von neuen Guanidinverbindungen
AT214427B (de)	1961-04-10	Verfahren zur Herstellung neuer basischer Phenoläther
DE922650C (de)	1955-01-20	Verfahren zur Herstellung von Bibenzothiazolabkoemmlingen bzw. deren Salzen
DE2236005C3 (de)	1976-07-08	Dibenzo- eckige Klammer auf d,f eckige Klammer zu -dioxepin- eckige Klammer auf 1,3 eckige Klammer zu -derivate und deren pharmakologisch verträgliche Salze, sowie Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE925467C (de)	1955-03-21	Verfahren zur Herstellung sekundaerer 3-Azapentylen-(1, 5)-bis-trialkyl-ammoniumverbindungen
AT257057B (de)	1967-09-25	Verfahren zur Herstellung von Bis-[4-hydroxymethyl-5-hydroxy-6-methyl-pyridyl-(3)-methyl]-disulfid
AT234698B (de)	1964-07-10	Verfahren zur Herstellung von 4-Sulfanilamido-2,6-di-nieder-alkoxy-pyrimidinen
AT214429B (de)	1961-04-10	Verfahren zur Herstellung neuer basischer Phenoläther