CH515908A - Verfahren zur Herstellung von 2-(Trichlorbenzyl)-2-imidazolinen - Google Patents
Verfahren zur Herstellung von 2-(Trichlorbenzyl)-2-imidazolinenInfo
- Publication number
- CH515908A CH515908A CH509468A CH509468A CH515908A CH 515908 A CH515908 A CH 515908A CH 509468 A CH509468 A CH 509468A CH 509468 A CH509468 A CH 509468A CH 515908 A CH515908 A CH 515908A
- Authority
- CH
- Switzerland
- Prior art keywords
- trichlorobenzyl
- imidazoline
- hydrochloric acid
- mice
- molecular weight
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 125000001309 chloro group Chemical group Cl* 0.000 title abstract description 4
- 150000001450 anions Chemical class 0.000 title abstract 2
- 241000699670 Mus sp. Species 0.000 claims abstract description 24
- 230000000202 analgesic effect Effects 0.000 claims abstract description 7
- 239000002934 diuretic Substances 0.000 claims abstract description 4
- 230000001882 diuretic effect Effects 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 29
- -1 2- (2,4,5-Trichlorobenzyl) -2-imidazoline tosylate Chemical compound 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- RZAARLYULZKCEK-UHFFFAOYSA-N 2-[(2,3,6-trichlorophenyl)methyl]-4,5-dihydro-1H-imidazole Chemical compound ClC1=C(CC=2NCCN2)C(=CC=C1Cl)Cl RZAARLYULZKCEK-UHFFFAOYSA-N 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 16
- AUSHSURJGODDIZ-UHFFFAOYSA-N 2-[(2,4,5-trichlorophenyl)methyl]-4,5-dihydro-1H-imidazole Chemical compound ClC1=C(CC=2NCCN2)C=C(C(=C1)Cl)Cl AUSHSURJGODDIZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- BWBZMVMNDZCZKZ-UHFFFAOYSA-N 1-methyl-2-[(2,3,6-trichlorophenyl)methyl]-4,5-dihydroimidazole Chemical compound CN1C(=NCC1)CC1=C(C(=CC=C1Cl)Cl)Cl BWBZMVMNDZCZKZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 8
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- CYPFPSICESWOSR-UHFFFAOYSA-N 2-(2,4,5-trichlorophenyl)acetonitrile Chemical compound ClC1=CC(Cl)=C(CC#N)C=C1Cl CYPFPSICESWOSR-UHFFFAOYSA-N 0.000 claims description 7
- 239000007928 intraperitoneal injection Substances 0.000 claims description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 5
- VVVRSNXQGMSWSV-UHFFFAOYSA-N 2-[(2,3,6-trichlorophenyl)methyl]-4,5-dihydro-1H-imidazole hydrochloride Chemical compound Cl.ClC1=C(CC=2NCCN2)C(=CC=C1Cl)Cl VVVRSNXQGMSWSV-UHFFFAOYSA-N 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- 239000001630 malic acid Substances 0.000 claims description 5
- 235000011090 malic acid Nutrition 0.000 claims description 5
- 230000000144 pharmacologic effect Effects 0.000 claims description 5
- VFFKSHPDBRNFPW-UHFFFAOYSA-N 2-[(2,4,5-trichlorophenyl)methyl]-4,5-dihydro-1H-imidazole hydrochloride Chemical compound Cl.ClC1=C(CC=2NCCN2)C=C(C(=C1)Cl)Cl VFFKSHPDBRNFPW-UHFFFAOYSA-N 0.000 claims description 4
- HVCCFMAPGCBCHZ-UHFFFAOYSA-N 2-aminoethylazanium;4-methylbenzenesulfonate Chemical compound NCCN.CC1=CC=C(S(O)(=O)=O)C=C1 HVCCFMAPGCBCHZ-UHFFFAOYSA-N 0.000 claims description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 4
- 238000002474 experimental method Methods 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000001384 succinic acid Substances 0.000 claims description 4
- KQWHNBIYSHFRLC-UHFFFAOYSA-N 2-(2,4,6-trichlorophenyl)acetonitrile Chemical compound ClC1=CC(Cl)=C(CC#N)C(Cl)=C1 KQWHNBIYSHFRLC-UHFFFAOYSA-N 0.000 claims description 3
- 241000699666 Mus <mouse, genus> Species 0.000 claims description 3
- 210000001015 abdomen Anatomy 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 3
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- 229940049920 malate Drugs 0.000 claims description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 3
- 210000004197 pelvis Anatomy 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 239000003204 tranquilizing agent Substances 0.000 claims description 3
- 230000002936 tranquilizing effect Effects 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 230000001773 anti-convulsant effect Effects 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 239000001961 anticonvulsive agent Substances 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 229960003965 antiepileptics Drugs 0.000 claims description 2
- 230000005587 bubbling Effects 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 claims description 2
- 229960002456 hexobarbital Drugs 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 230000003389 potentiating effect Effects 0.000 claims description 2
- 230000004622 sleep time Effects 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 2
- 229940125725 tranquilizer Drugs 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 abstract description 2
- 239000000730 antalgic agent Substances 0.000 abstract description 2
- 229940030606 diuretics Drugs 0.000 abstract description 2
- 231100000957 no side effect Toxicity 0.000 abstract 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000012458 free base Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000002462 imidazolines Chemical class 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229940025084 amphetamine Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZUZLGSONCFESPE-UHFFFAOYSA-N 2-(2,3,6-trichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(Cl)C(CC#N)=C1Cl ZUZLGSONCFESPE-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 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
- 150000001298 alcohols Chemical class 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DDJWQUFEOMNFKJ-UHFFFAOYSA-N 1-methyl-2-[(2,3,6-trichlorophenyl)methyl]-4,5-dihydroimidazole hydrochloride Chemical compound Cl.CN1C(=NCC1)CC1=C(C(=CC=C1Cl)Cl)Cl DDJWQUFEOMNFKJ-UHFFFAOYSA-N 0.000 description 1
- VHBUHVHHNRJLAS-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.ClC1=C(CC=2NCCN2)C(=CC=C1Cl)Cl Chemical compound C(C=C/C(=O)O)(=O)O.ClC1=C(CC=2NCCN2)C(=CC=C1Cl)Cl VHBUHVHHNRJLAS-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
- 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
- 206010044565 Tremor Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000012431 aqueous reaction media Substances 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
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 238000007069 methylation reaction Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- LZJLROCGDZZRMC-UHFFFAOYSA-N sulfuric acid 2-[(2,3,6-trichlorophenyl)methyl]-4,5-dihydro-1H-imidazole Chemical compound S(=O)(=O)(O)O.ClC1=C(CC=2NCCN2)C(=CC=C1Cl)Cl LZJLROCGDZZRMC-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62829867A | 1967-04-04 | 1967-04-04 | |
| US62830567A | 1967-04-04 | 1967-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH515908A true CH515908A (de) | 1971-11-30 |
Family
ID=27090673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH509468A CH515908A (de) | 1967-04-04 | 1968-04-04 | Verfahren zur Herstellung von 2-(Trichlorbenzyl)-2-imidazolinen |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US3423422A (en:Method) |
| BE (1) | BE713193A (en:Method) |
| CH (1) | CH515908A (en:Method) |
| DE (1) | DE1770114A1 (en:Method) |
| DK (1) | DK115776B (en:Method) |
| FR (2) | FR1580194A (en:Method) |
| GB (1) | GB1165099A (en:Method) |
| NL (1) | NL6804671A (en:Method) |
| NO (1) | NO121664B (en:Method) |
| SE (1) | SE342452B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2359816A1 (de) * | 1972-11-30 | 1974-06-06 | Hexachimie | 1-(2-delta hoch 2-imidazolinyl)-2,2diarylcyclopropane und verfahren zu ihrer herstellung |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20230312524A1 (en) * | 2020-08-27 | 2023-10-05 | Curasen Therapeutics, Inc. | Alpha1a-adrenergic receptor agonists and methods of use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2919274A (en) * | 1957-09-17 | 1959-12-29 | Sahyun Melville | Amidines |
-
1967
- 1967-04-04 US US628298A patent/US3423422A/en not_active Expired - Lifetime
- 1967-04-04 US US628305A patent/US3423423A/en not_active Expired - Lifetime
-
1968
- 1968-03-22 NO NO1118/68A patent/NO121664B/no unknown
- 1968-03-29 FR FR1580194D patent/FR1580194A/fr not_active Expired
- 1968-04-01 SE SE4281/68A patent/SE342452B/xx unknown
- 1968-04-02 DE DE19681770114 patent/DE1770114A1/de active Pending
- 1968-04-02 GB GB05809/68A patent/GB1165099A/en not_active Expired
- 1968-04-03 BE BE713193D patent/BE713193A/xx unknown
- 1968-04-03 NL NL6804671A patent/NL6804671A/xx unknown
- 1968-04-03 DK DK147368AA patent/DK115776B/da unknown
- 1968-04-04 CH CH509468A patent/CH515908A/de not_active IP Right Cessation
- 1968-06-28 FR FR157206A patent/FR8077M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2359816A1 (de) * | 1972-11-30 | 1974-06-06 | Hexachimie | 1-(2-delta hoch 2-imidazolinyl)-2,2diarylcyclopropane und verfahren zu ihrer herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| BE713193A (en:Method) | 1968-10-03 |
| NL6804671A (en:Method) | 1968-10-07 |
| DK115776B (da) | 1969-11-10 |
| FR8077M (en:Method) | 1970-07-15 |
| DE1770114A1 (de) | 1971-09-23 |
| GB1165099A (en) | 1969-09-24 |
| US3423422A (en) | 1969-01-21 |
| US3423423A (en) | 1969-01-21 |
| NO121664B (en:Method) | 1971-03-29 |
| FR1580194A (en:Method) | 1969-09-05 |
| SE342452B (en:Method) | 1972-02-07 |
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