DE2037319C3 - Amindenvate des 1,4 Athano 1,2,3, 4 tetrahydro 5 naphtols und deren Salze, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate - Google Patents
Amindenvate des 1,4 Athano 1,2,3, 4 tetrahydro 5 naphtols und deren Salze, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische PräparateInfo
- Publication number
- DE2037319C3 DE2037319C3 DE19702037319 DE2037319A DE2037319C3 DE 2037319 C3 DE2037319 C3 DE 2037319C3 DE 19702037319 DE19702037319 DE 19702037319 DE 2037319 A DE2037319 A DE 2037319A DE 2037319 C3 DE2037319 C3 DE 2037319C3
- Authority
- DE
- Germany
- Prior art keywords
- compound
- salts
- ethano
- tetrahydro
- athano
- 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
- 150000003839 salts Chemical class 0.000 title description 9
- 238000000034 method Methods 0.000 title description 3
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001412 amines Chemical class 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 23
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 229960003712 propranolol Drugs 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229940039009 isoproterenol Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-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
- 229910010082 LiAlH Inorganic materials 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GRCBPHUNBYTWRP-UHFFFAOYSA-N 1,8,9,10,11,12-hexahydrotricyclo[6.2.2.0^{2,7}]dodeca-3,9-dien-3-ol Chemical compound C1CC2CCC1C1=C2C=CC=C1O GRCBPHUNBYTWRP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241001366338 Celastrina echo Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 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 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010067598 Neurogenic hypertension Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000674 adrenergic antagonist Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2027869 | 1969-07-30 | ||
| IT2019370 | 1970-02-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2037319A1 DE2037319A1 (de) | 1971-02-11 |
| DE2037319B2 DE2037319B2 (de) | 1973-04-26 |
| DE2037319C3 true DE2037319C3 (de) | 1973-11-22 |
Family
ID=26327437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702037319 Expired DE2037319C3 (de) | 1969-07-30 | 1970-07-28 | Amindenvate des 1,4 Athano 1,2,3, 4 tetrahydro 5 naphtols und deren Salze, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5010591B1 (enExample) |
| AT (1) | AT303700B (enExample) |
| BE (1) | BE753917A (enExample) |
| CH (1) | CH539017A (enExample) |
| CS (1) | CS163218B2 (enExample) |
| DE (1) | DE2037319C3 (enExample) |
| ES (1) | ES382297A1 (enExample) |
| FR (1) | FR2059580B1 (enExample) |
| GB (1) | GB1263035A (enExample) |
| IE (1) | IE34394B1 (enExample) |
| NL (1) | NL7011244A (enExample) |
| NO (1) | NO129042B (enExample) |
| SE (1) | SE368820B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1436860A (en) * | 1972-12-18 | 1976-05-26 | Syntex Inc | 5,8-dihydro-5,8-methanonaphthalene cardiovascular agents |
-
1970
- 1970-07-17 IE IE93470A patent/IE34394B1/xx unknown
- 1970-07-22 GB GB3555070A patent/GB1263035A/en not_active Expired
- 1970-07-24 BE BE753917D patent/BE753917A/xx unknown
- 1970-07-27 AT AT685570A patent/AT303700B/de not_active IP Right Cessation
- 1970-07-28 DE DE19702037319 patent/DE2037319C3/de not_active Expired
- 1970-07-29 SE SE1040070A patent/SE368820B/xx unknown
- 1970-07-29 ES ES382297A patent/ES382297A1/es not_active Expired
- 1970-07-29 NL NL7011244A patent/NL7011244A/xx unknown
- 1970-07-29 NO NO294470A patent/NO129042B/no unknown
- 1970-07-30 CS CS534870A patent/CS163218B2/cs unknown
- 1970-07-30 FR FR7028201A patent/FR2059580B1/fr not_active Expired
- 1970-07-30 JP JP6646970A patent/JPS5010591B1/ja active Pending
- 1970-07-30 CH CH1153170A patent/CH539017A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1263035A (en) | 1972-02-09 |
| AT303700B (de) | 1972-12-11 |
| DE2037319A1 (de) | 1971-02-11 |
| ES382297A1 (es) | 1973-04-16 |
| NL7011244A (enExample) | 1971-02-02 |
| IE34394L (en) | 1971-01-30 |
| NO129042B (enExample) | 1974-02-18 |
| BE753917A (fr) | 1971-01-25 |
| FR2059580A1 (enExample) | 1971-06-04 |
| CH539017A (de) | 1973-07-15 |
| FR2059580B1 (enExample) | 1973-12-21 |
| IE34394B1 (en) | 1975-04-30 |
| SE368820B (enExample) | 1974-07-22 |
| CS163218B2 (enExample) | 1975-08-29 |
| JPS5010591B1 (enExample) | 1975-04-22 |
| DE2037319B2 (de) | 1973-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |