DE2001431C3 - 2-(2'-Hydroxy-3'-alkylaminopropoxy)-Omega-phenyl-propiophenone und Verfahren zur Herstellung derselben - Google Patents
2-(2'-Hydroxy-3'-alkylaminopropoxy)-Omega-phenyl-propiophenone und Verfahren zur Herstellung derselbenInfo
- Publication number
- DE2001431C3 DE2001431C3 DE19702001431 DE2001431A DE2001431C3 DE 2001431 C3 DE2001431 C3 DE 2001431C3 DE 19702001431 DE19702001431 DE 19702001431 DE 2001431 A DE2001431 A DE 2001431A DE 2001431 C3 DE2001431 C3 DE 2001431C3
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- phenyl
- propiophenones
- alkylaminopropoxy
- same
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010003119 arrhythmia Diseases 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 238000010253 intravenous injection Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- -1 1 henytoin Chemical compound 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960000244 procainamide Drugs 0.000 description 2
- REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 description 1
- GJHKWLSRHNWTAN-UHFFFAOYSA-N 1-ethoxy-4-(4-pentylcyclohexyl)benzene Chemical compound C1CC(CCCCC)CCC1C1=CC=C(OCC)C=C1 GJHKWLSRHNWTAN-UHFFFAOYSA-N 0.000 description 1
- XANXPGVXSBTDEK-UHFFFAOYSA-N 2-hydroxy-1-(3-phenylphenyl)propan-1-one Chemical compound OC(C(=O)C1=CC=CC(=C1)C1=CC=CC=C1)C XANXPGVXSBTDEK-UHFFFAOYSA-N 0.000 description 1
- RIRLTTUCUAODRW-UHFFFAOYSA-N 2-methylpropan-2-amine;propan-1-amine Chemical compound CCCN.CC(C)(C)N RIRLTTUCUAODRW-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 239000001576 FEMA 2977 Substances 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 241000276489 Merlangius merlangus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000001435 haemodynamic effect Effects 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229960004215 prajmaline Drugs 0.000 description 1
- UAUHEPXILIZYCU-ALHOSYKFSA-N prajmalium Chemical compound CN([C@H]12)C3=CC=CC=C3[C@]11C[C@@H]3[N@@+](CCC)([C@@H]([C@H]4CC)O)[C@H]2C[C@@H]4[C@@H]3[C@H]1O UAUHEPXILIZYCU-ALHOSYKFSA-N 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 229960004482 quinidine sulfate Drugs 0.000 description 1
- 229960003110 quinine sulfate Drugs 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702001431 DE2001431C3 (de) | 1970-01-06 | 1970-01-06 | 2-(2'-Hydroxy-3'-alkylaminopropoxy)-Omega-phenyl-propiophenone und Verfahren zur Herstellung derselben |
| ES392962A ES392962A1 (es) | 1970-01-06 | 1971-07-06 | Procedimiento para la preparacion de derivados de la 2' hi-droxi-3-fenilpropiofenona. |
| YU176571A YU35340B (en) | 1970-01-06 | 1971-07-06 | Process for obtaining novel 0-(2-hydroxy-3-alklaminopropoxy)-beta-phenylpropiophenones |
| FR7124903A FR2144601B1 (OSRAM) | 1970-01-06 | 1971-07-07 | |
| GB1307455D GB1307455A (en) | 1970-01-06 | 1971-07-07 | 2,-hydroxy-3-phenylpropiophenone derivatives |
| AT591871A AT308076B (de) | 1970-01-06 | 1971-07-07 | Verfahren zur Herstellung neuer o-(2'-Hydroxy-3'-alkylaminopropoxy)-β-phenylpropiophenone und deren Salze |
| NL7208214A NL7208214A (OSRAM) | 1970-01-06 | 1972-06-15 | |
| BE785318A BE785318A (fr) | 1970-01-06 | 1972-06-23 | Procede de preparation de nouveaux derives therapeutiques de l'hydroxy-2' phenyl-3 propiophenone et de leurs sels |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702001431 DE2001431C3 (de) | 1970-01-06 | 1970-01-06 | 2-(2'-Hydroxy-3'-alkylaminopropoxy)-Omega-phenyl-propiophenone und Verfahren zur Herstellung derselben |
| FR7124903A FR2144601B1 (OSRAM) | 1970-01-06 | 1971-07-07 | |
| GB3198471 | 1971-07-07 | ||
| AT591871A AT308076B (de) | 1970-01-06 | 1971-07-07 | Verfahren zur Herstellung neuer o-(2'-Hydroxy-3'-alkylaminopropoxy)-β-phenylpropiophenone und deren Salze |
| NL7208214A NL7208214A (OSRAM) | 1970-01-06 | 1972-06-15 | |
| BE785318A BE785318A (fr) | 1970-01-06 | 1972-06-23 | Procede de preparation de nouveaux derives therapeutiques de l'hydroxy-2' phenyl-3 propiophenone et de leurs sels |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2001431A1 DE2001431A1 (de) | 1971-07-15 |
| DE2001431B2 DE2001431B2 (de) | 1974-05-09 |
| DE2001431C3 true DE2001431C3 (de) | 1974-12-12 |
Family
ID=27542486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702001431 Expired DE2001431C3 (de) | 1970-01-06 | 1970-01-06 | 2-(2'-Hydroxy-3'-alkylaminopropoxy)-Omega-phenyl-propiophenone und Verfahren zur Herstellung derselben |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT308076B (OSRAM) |
| BE (1) | BE785318A (OSRAM) |
| DE (1) | DE2001431C3 (OSRAM) |
| FR (1) | FR2144601B1 (OSRAM) |
| GB (1) | GB1307455A (OSRAM) |
| NL (1) | NL7208214A (OSRAM) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3226863A1 (de) | 1981-09-18 | 1983-04-07 | Basf Ag, 6700 Ludwigshafen | Aminopropanolderivate von 2-hydroxy-ss-phenyl-propiophenonen, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| DE3328376A1 (de) * | 1983-07-21 | 1985-01-31 | Helopharm W. Petrik & Co Kg, 1000 Berlin | Aminopropanolderivate von 2-hydroxy-ss-phenyl-propiophenonen, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| DE3429667A1 (de) * | 1984-08-11 | 1986-02-20 | Knoll Ag, 6700 Ludwigshafen | Verfahren zur herstellung von substituierten aryl-alkylketonen |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL48309A (en) * | 1974-10-25 | 1980-01-31 | Robins Co Inc A H | 1-aryloxy-4-amino-2-butanols and pharmaceutical compositions containing them |
| JPS5832847A (ja) * | 1981-08-20 | 1983-02-25 | Mitsubishi Chem Ind Ltd | （３−アミノプロポキシ）ビベンジル類 |
| DE3133814C2 (de) * | 1981-08-25 | 1983-12-22 | Helopharm W. Petrik & Co Kg, 1000 Berlin | 2-[2'-Hydroxy-3'-(1,1-dimethylpropylamino)-propoxy]-β-phenylpropiophenon, seine Säureadditionssalze und Arzneimittel |
| DE3210061A1 (de) * | 1982-03-19 | 1983-09-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von propafenon |
| US4540697A (en) * | 1982-09-09 | 1985-09-10 | Basf Aktiengesellschaft | Aminopropanol derivatives of 2-hydroxy-β-phenyl-propiophenones, pharmaceutical compositions and use |
| DE3309595A1 (de) * | 1983-03-17 | 1984-09-20 | Basf Ag, 6700 Ludwigshafen | Neue aminopropanolderivate von 1-(2-hydroxy-phenyl)-3-phenyl-propanolen, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| DE3343671A1 (de) * | 1983-12-02 | 1985-06-20 | Basf Ag, 6700 Ludwigshafen | Aminopropanolderivate von substituierten 2-hydroxy-propiophenonen, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| DE3907512C2 (de) * | 1989-03-08 | 1997-08-14 | Laevosan Gmbh & Co Kg | Neue Aryloxy-alkylamine, deren Herstellung und diese enthaltende Arzneimittel |
| DE3911069A1 (de) * | 1989-04-06 | 1990-10-11 | Knoll Ag | Einkristalle von ss-phenylpropiophenonen |
| DE4000213A1 (de) * | 1990-01-05 | 1991-07-11 | Helopharm Petrik Co Kg | O-hydroxy-ss-(1-naphthyl)-propiophenonderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| JP2766073B2 (ja) | 1990-04-04 | 1998-06-18 | クノル アクチェンゲゼルシャフト | β―フェニルプロピオフェノンの単結晶 |
-
1970
- 1970-01-06 DE DE19702001431 patent/DE2001431C3/de not_active Expired
-
1971
- 1971-07-07 GB GB1307455D patent/GB1307455A/en not_active Expired
- 1971-07-07 AT AT591871A patent/AT308076B/de not_active IP Right Cessation
- 1971-07-07 FR FR7124903A patent/FR2144601B1/fr not_active Expired
-
1972
- 1972-06-15 NL NL7208214A patent/NL7208214A/xx not_active Application Discontinuation
- 1972-06-23 BE BE785318A patent/BE785318A/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3226863A1 (de) | 1981-09-18 | 1983-04-07 | Basf Ag, 6700 Ludwigshafen | Aminopropanolderivate von 2-hydroxy-ss-phenyl-propiophenonen, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| DE3328376A1 (de) * | 1983-07-21 | 1985-01-31 | Helopharm W. Petrik & Co Kg, 1000 Berlin | Aminopropanolderivate von 2-hydroxy-ss-phenyl-propiophenonen, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| DE3429667A1 (de) * | 1984-08-11 | 1986-02-20 | Knoll Ag, 6700 Ludwigshafen | Verfahren zur herstellung von substituierten aryl-alkylketonen |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2144601B1 (OSRAM) | 1974-08-02 |
| BE785318A (fr) | 1972-10-16 |
| DE2001431A1 (de) | 1971-07-15 |
| NL7208214A (OSRAM) | 1973-12-18 |
| FR2144601A1 (OSRAM) | 1973-02-16 |
| DE2001431B2 (de) | 1974-05-09 |
| GB1307455A (en) | 1973-02-21 |
| AT308076B (de) | 1973-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |