DE1122544B - Verfahren zur Herstellung neuer histaminantagonistisch wirksamer Aminoalkylaether - Google Patents
Verfahren zur Herstellung neuer histaminantagonistisch wirksamer AminoalkylaetherInfo
- Publication number
- DE1122544B DE1122544B DEA32142A DEA0032142A DE1122544B DE 1122544 B DE1122544 B DE 1122544B DE A32142 A DEA32142 A DE A32142A DE A0032142 A DEA0032142 A DE A0032142A DE 1122544 B DE1122544 B DE 1122544B
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- methyl
- preparation
- benzhydrol
- histamine
- Prior art date
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 229940066768 systemic antihistamines aminoalkyl ethers Drugs 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 16
- 230000001078 anti-cholinergic effect Effects 0.000 claims description 10
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- -1 -isopropyl halide Chemical class 0.000 claims description 4
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001860 citric acid derivatives Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229930003347 Atropine Natural products 0.000 description 5
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 5
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 5
- 229960000396 atropine Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 229960001789 papaverine Drugs 0.000 description 3
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000956 myotropic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZJWLZKFJGOATHR-UHFFFAOYSA-N 1-(2-chloropropan-2-yl)piperidine Chemical compound CC(C)(Cl)N1CCCCC1 ZJWLZKFJGOATHR-UHFFFAOYSA-N 0.000 description 1
- CSNDXIYFXVAWEY-UHFFFAOYSA-N 1-chloro-4-[1-[1-(4-chlorophenyl)-1-phenylethoxy]-1-phenylethyl]benzene Chemical compound ClC1=CC=C(C(C2=CC=CC=C2)(C)OC(C2=CC=C(C=C2)Cl)(C2=CC=CC=C2)C)C=C1 CSNDXIYFXVAWEY-UHFFFAOYSA-N 0.000 description 1
- QDWYBBAEFXJZLZ-UHFFFAOYSA-N 2-chloro-n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)(C)Cl QDWYBBAEFXJZLZ-UHFFFAOYSA-N 0.000 description 1
- GIGKDZSQVOYRKV-UHFFFAOYSA-N 4-(2-chloropropan-2-yl)morpholine Chemical compound O1CCN(CC1)C(C)(C)Cl GIGKDZSQVOYRKV-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229960000520 diphenhydramine Drugs 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000079 pharmacotherapeutic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL252001D NL252001A (en, 2012) | 1959-05-30 | ||
| DEA32142A DE1122544B (de) | 1959-05-30 | 1959-05-30 | Verfahren zur Herstellung neuer histaminantagonistisch wirksamer Aminoalkylaether |
| BE591071A BE591071A (fr) | 1959-05-30 | 1960-05-20 | Procédé de préparation d'ethers amino-alcoyliques d'alcools de la serie aromatique-aliphatique. |
| CH603060A CH386448A (de) | 1959-05-30 | 1960-05-25 | Verfahren zur Herstellung von Aminoalkyläthern von Alkoholen der aromatisch-aliphatischen Reihe |
| GB18840/60A GB875060A (en) | 1959-05-30 | 1960-05-27 | N,n-disubstituted ª--aminoalkylethers of alcohols of the aromatic-aliphatic series and a process for the production thereof |
| FR828484A FR280M (fr) | 1959-05-30 | 1960-08-24 | Éther aminoalcoylique d'alcool de la série aromatique-aliphatique. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA32142A DE1122544B (de) | 1959-05-30 | 1959-05-30 | Verfahren zur Herstellung neuer histaminantagonistisch wirksamer Aminoalkylaether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1122544B true DE1122544B (de) | 1962-01-25 |
Family
ID=6927707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA32142A Pending DE1122544B (de) | 1959-05-30 | 1959-05-30 | Verfahren zur Herstellung neuer histaminantagonistisch wirksamer Aminoalkylaether |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE591071A (en, 2012) |
| CH (1) | CH386448A (en, 2012) |
| DE (1) | DE1122544B (en, 2012) |
| FR (1) | FR280M (en, 2012) |
| GB (1) | GB875060A (en, 2012) |
| NL (1) | NL252001A (en, 2012) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1094069A (fr) * | 1953-08-24 | 1955-05-11 | Fond D Equipement De L Hygiene | Procédé d'obtention d'éthers-oxydes de benzhydrols et d'aminoalcools |
-
0
- NL NL252001D patent/NL252001A/xx unknown
-
1959
- 1959-05-30 DE DEA32142A patent/DE1122544B/de active Pending
-
1960
- 1960-05-20 BE BE591071A patent/BE591071A/fr unknown
- 1960-05-25 CH CH603060A patent/CH386448A/de unknown
- 1960-05-27 GB GB18840/60A patent/GB875060A/en not_active Expired
- 1960-08-24 FR FR828484A patent/FR280M/fr active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1094069A (fr) * | 1953-08-24 | 1955-05-11 | Fond D Equipement De L Hygiene | Procédé d'obtention d'éthers-oxydes de benzhydrols et d'aminoalcools |
Also Published As
| Publication number | Publication date |
|---|---|
| FR280M (fr) | 1961-03-13 |
| BE591071A (fr) | 1960-09-16 |
| CH386448A (de) | 1965-01-15 |
| GB875060A (en) | 1961-08-16 |
| NL252001A (en, 2012) |
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