DE1180365B - Verfahren zur Herstellung von Alkylammonium-Campher-10-sulfonaten - Google Patents
Verfahren zur Herstellung von Alkylammonium-Campher-10-sulfonatenInfo
- Publication number
- DE1180365B DE1180365B DEA42637A DEA0042637A DE1180365B DE 1180365 B DE1180365 B DE 1180365B DE A42637 A DEA42637 A DE A42637A DE A0042637 A DEA0042637 A DE A0042637A DE 1180365 B DE1180365 B DE 1180365B
- Authority
- DE
- Germany
- Prior art keywords
- camphor
- alkylammonium
- sulfonates
- preparation
- sulfonic acid
- 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 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 alkylammonium camphor-10-sulfonates Chemical class 0.000 title description 8
- 150000003839 salts Chemical class 0.000 claims description 9
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical class CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- IJUZWPVVLRFXDI-UHFFFAOYSA-N (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;6-methylheptan-2-ylazanium Chemical compound CC(C)CCCC(C)N.C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C IJUZWPVVLRFXDI-UHFFFAOYSA-N 0.000 description 3
- LREQLEBVOXIEOM-UHFFFAOYSA-N 6-amino-2-methyl-2-heptanol Chemical compound CC(N)CCCC(C)(C)O LREQLEBVOXIEOM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000001953 Hypotension Diseases 0.000 description 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000036543 hypotension Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
- MKMYPTLXLWOUSO-NFQNBQCWSA-N 2-[(2r,6s)-6-[(2s)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;hydrochloride Chemical compound Cl.C1([C@@H](O)C[C@H]2N([C@H](CCC2)CC(=O)C=2C=CC=CC=2)C)=CC=CC=C1 MKMYPTLXLWOUSO-NFQNBQCWSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 241001071864 Lethrinus laticaudis Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 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
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229960005402 heptaminol Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XJKNEUMPYCZDKU-FHZGLPGMSA-N (2r,3r)-2,3-dihydroxy-4-[4-[1-hydroxy-2-(methylamino)ethyl]phenoxy]-4-oxobutanoic acid Chemical compound CNCC(O)C1=CC=C(OC(=O)[C@H](O)[C@@H](O)C(O)=O)C=C1 XJKNEUMPYCZDKU-FHZGLPGMSA-N 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- BALXUFOVQVENIU-GNAZCLTHSA-N Ephedrine hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-GNAZCLTHSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical class CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010043087 Tachyphylaxis Diseases 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 229960002534 ephedrine hydrochloride Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000026781 habituation Effects 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
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- QNIVIMYXGGFTAK-UHFFFAOYSA-N octodrine Chemical compound CC(C)CCCC(C)N QNIVIMYXGGFTAK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002746 orthostatic effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA42637A DE1180365B (de) | 1963-03-19 | 1963-03-19 | Verfahren zur Herstellung von Alkylammonium-Campher-10-sulfonaten |
| FR967934A FR4156M (cs) | 1963-03-19 | 1964-03-19 | |
| BR15772264A BR6457722D0 (pt) | 1963-03-19 | 1964-03-19 | Processo de preparacao de novos canfora-sulfonatos de acao terapeutica |
| NL6402943A NL6402943A (cs) | 1963-03-19 | 1964-03-19 | |
| BE645452D BE645452A (cs) | 1963-03-19 | 1964-03-19 | |
| SE343364A SE316168B (cs) | 1963-03-19 | 1964-03-19 | |
| GB11720/64A GB1011317A (en) | 1963-03-19 | 1964-03-19 | Therapeutically active camphor sulphonates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA42637A DE1180365B (de) | 1963-03-19 | 1963-03-19 | Verfahren zur Herstellung von Alkylammonium-Campher-10-sulfonaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1180365B true DE1180365B (de) | 1964-10-29 |
Family
ID=6933203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA42637A Pending DE1180365B (de) | 1963-03-19 | 1963-03-19 | Verfahren zur Herstellung von Alkylammonium-Campher-10-sulfonaten |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE645452A (cs) |
| BR (1) | BR6457722D0 (cs) |
| DE (1) | DE1180365B (cs) |
| FR (1) | FR4156M (cs) |
| GB (1) | GB1011317A (cs) |
| NL (1) | NL6402943A (cs) |
| SE (1) | SE316168B (cs) |
-
1963
- 1963-03-19 DE DEA42637A patent/DE1180365B/de active Pending
-
1964
- 1964-03-19 GB GB11720/64A patent/GB1011317A/en not_active Expired
- 1964-03-19 NL NL6402943A patent/NL6402943A/xx unknown
- 1964-03-19 FR FR967934A patent/FR4156M/fr not_active Expired
- 1964-03-19 BE BE645452D patent/BE645452A/xx unknown
- 1964-03-19 BR BR15772264A patent/BR6457722D0/pt unknown
- 1964-03-19 SE SE343364A patent/SE316168B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6457722D0 (pt) | 1973-07-17 |
| NL6402943A (cs) | 1964-09-21 |
| BE645452A (cs) | 1964-07-16 |
| SE316168B (cs) | 1969-10-20 |
| GB1011317A (en) | 1965-11-24 |
| FR4156M (cs) | 1966-05-16 |
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