DD141157A1 - Verfahren zur herstellung von neuen arylaminoimidazolinderivaten - Google Patents
Verfahren zur herstellung von neuen arylaminoimidazolinderivaten Download PDFInfo
- Publication number
- DD141157A1 DD141157A1 DD78210199A DD21019978A DD141157A1 DD 141157 A1 DD141157 A1 DD 141157A1 DD 78210199 A DD78210199 A DD 78210199A DD 21019978 A DD21019978 A DD 21019978A DD 141157 A1 DD141157 A1 DD 141157A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- compound
- imidazoline
- acid
- iii
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 30
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- -1 alkyl radical Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000001077 hypotensive effect Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical class C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 description 5
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 229960002896 clonidine Drugs 0.000 description 3
- CXWMHIRIXVNVQN-UHFFFAOYSA-N cyclohex-3-ene-1-carbonyl chloride Chemical compound ClC(=O)C1CCC=CC1 CXWMHIRIXVNVQN-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- VWOMPABUYLIFCY-UHFFFAOYSA-N cyclohex-3-ene-1-carbonyl cyclohex-3-ene-1-carboxylate Chemical compound C1CC=CCC1C(=O)OC(=O)C1CCC=CC1 VWOMPABUYLIFCY-UHFFFAOYSA-N 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LFDGRWDETVOGDT-UHFFFAOYSA-N 1h-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 description 1
- JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- SACAEVOKRBNXPN-UHFFFAOYSA-N n-phenyl-4,5-dihydroimidazol-1-amine Chemical class C1=NCCN1NC1=CC=CC=C1 SACAEVOKRBNXPN-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C07D233/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- C07D233/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782811847 DE2811847A1 (de) | 1978-03-17 | 1978-03-17 | Neue arylaminoimidazolinderivate, deren herstellung und verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD141157A1 true DD141157A1 (de) | 1980-04-16 |
Family
ID=6034806
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78210199A DD141157A1 (de) | 1978-03-17 | 1978-12-27 | Verfahren zur herstellung von neuen arylaminoimidazolinderivaten |
| DD78210201A DD141158A1 (de) | 1978-03-17 | 1978-12-27 | Verfahren zur herstellung von neuen arylaminoimidazolinderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78210201A DD141158A1 (de) | 1978-03-17 | 1978-12-27 | Verfahren zur herstellung von neuen arylaminoimidazolinderivaten |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4142051A (cs) |
| EP (1) | EP0004529B1 (cs) |
| JP (1) | JPS54128570A (cs) |
| AU (1) | AU521523B2 (cs) |
| CA (2) | CA1107285A (cs) |
| CS (2) | CS203026B2 (cs) |
| DD (2) | DD141157A1 (cs) |
| DE (2) | DE2811847A1 (cs) |
| DK (1) | DK569078A (cs) |
| ES (2) | ES476355A1 (cs) |
| FI (1) | FI784017A7 (cs) |
| GR (2) | GR64429B (cs) |
| HU (1) | HU179219B (cs) |
| IL (1) | IL56075A (cs) |
| NO (1) | NO784423L (cs) |
| NZ (1) | NZ189279A (cs) |
| PT (2) | PT68988A (cs) |
| ZA (1) | ZA787312B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MTP837B (en) * | 1977-11-07 | 1979-10-22 | Hoffman La Roche And Co Aktien | Derivatives 2 finino-imidazolidire |
| DE3200258A1 (de) * | 1982-01-07 | 1983-07-21 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Substituierte 1-benzoyl-2-phenylimino-imidazolidine, deren saeureadditionssalze, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| JPS5922714U (ja) * | 1982-08-04 | 1984-02-13 | 藤徳紙器株式会社 | 紙製容器 |
| JPS5922715U (ja) * | 1982-08-04 | 1984-02-13 | 藤徳紙器株式会社 | 紙製容器 |
| JPS5935321U (ja) * | 1982-08-30 | 1984-03-05 | 株式会社岡田 | 紙製容器の側板構造 |
| DE19514579A1 (de) * | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE741947A (en) | 1969-11-19 | 1970-05-04 | N-acyl-2-arylamino-imidazoline | |
| DE2041732A1 (de) * | 1970-08-22 | 1972-02-24 | Bayer Ag | Acylierte Arylhydrazino-2-imidazoline,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasitizide |
| BE787683A (fr) * | 1971-08-20 | 1973-02-19 | Boehringer Sohn Ingelheim | 2-phenylimino-imidazolidines, leurs sels d'addition avec des acides et procedes pour les fabriquer |
| DE2316377C3 (de) * | 1973-04-02 | 1978-11-02 | Lentia Gmbh, Chem. U. Pharm. Erzeugnisse - Industriebedarf, 8000 Muenchen | Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen |
| AT330769B (de) | 1974-04-05 | 1976-07-26 | Chemie Linz Ag | Verfahren zur herstellung von 2-arylamino- 2-imidazolin-derivaten und ihren salzen |
| AT333749B (de) | 1974-07-03 | 1976-12-10 | Chemie Linz Ag | Verfahren zur herstellung von neuen 2-arylamino-2-imidazolinderivaten |
| AT339897B (de) * | 1975-09-25 | 1977-11-10 | Chemie Linz Ag | Verfahren zur herstellung des neuen 1-benzoyl-2- (2',6'-dichlorphenylamino) -2-imidazolins und von dessen salzen |
| DE2542702C2 (de) | 1975-09-25 | 1983-11-10 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur Herstellung von 1-Benzoyl-2-(2,6-dichlorphenylamino)-2-imidazolin |
-
1978
- 1978-03-17 DE DE19782811847 patent/DE2811847A1/de not_active Withdrawn
- 1978-04-20 US US05/898,543 patent/US4142051A/en not_active Expired - Lifetime
- 1978-11-29 IL IL56075A patent/IL56075A/xx unknown
- 1978-12-05 EP EP78101569A patent/EP0004529B1/de not_active Expired
- 1978-12-05 DE DE7878101569T patent/DE2860796D1/de not_active Expired
- 1978-12-06 CA CA317,503A patent/CA1107285A/en not_active Expired
- 1978-12-06 CA CA317,502A patent/CA1100513A/en not_active Expired
- 1978-12-16 GR GR57906A patent/GR64429B/el unknown
- 1978-12-16 GR GR57905A patent/GR64428B/el unknown
- 1978-12-18 CS CS788522A patent/CS203026B2/cs unknown
- 1978-12-18 CS CS788521A patent/CS200160B2/cs unknown
- 1978-12-19 DK DK569078A patent/DK569078A/da not_active Application Discontinuation
- 1978-12-21 NZ NZ189279A patent/NZ189279A/xx unknown
- 1978-12-26 JP JP15940078A patent/JPS54128570A/ja active Granted
- 1978-12-27 ZA ZA00787312A patent/ZA787312B/xx unknown
- 1978-12-27 DD DD78210199A patent/DD141157A1/de unknown
- 1978-12-27 PT PT68988A patent/PT68988A/pt unknown
- 1978-12-27 ES ES476355A patent/ES476355A1/es not_active Expired
- 1978-12-27 ES ES476354A patent/ES476354A1/es not_active Expired
- 1978-12-27 DD DD78210201A patent/DD141158A1/de unknown
- 1978-12-27 PT PT68989A patent/PT68989A/pt unknown
- 1978-12-28 FI FI784017A patent/FI784017A7/fi unknown
- 1978-12-28 AU AU42945/78A patent/AU521523B2/en not_active Expired
- 1978-12-29 NO NO784423A patent/NO784423L/no unknown
- 1978-12-29 HU HU78LI336A patent/HU179219B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS203026B2 (en) | 1981-02-27 |
| DE2860796D1 (en) | 1981-09-24 |
| IL56075A0 (en) | 1979-01-31 |
| PT68988A (de) | 1979-01-01 |
| JPS54128570A (en) | 1979-10-05 |
| GR64429B (en) | 1980-03-21 |
| IL56075A (en) | 1982-01-31 |
| NZ189279A (en) | 1980-08-26 |
| PT68989A (de) | 1979-01-01 |
| EP0004529A2 (de) | 1979-10-17 |
| AU4294578A (en) | 1979-09-20 |
| CS200160B2 (en) | 1980-08-29 |
| GR64428B (en) | 1980-03-21 |
| FI784017A7 (fi) | 1979-09-18 |
| CA1100513A (en) | 1981-05-05 |
| DK569078A (da) | 1979-09-18 |
| EP0004529A3 (en) | 1979-11-14 |
| ES476354A1 (es) | 1979-05-16 |
| ES476355A1 (es) | 1979-07-01 |
| NO784423L (no) | 1979-09-18 |
| EP0004529B1 (de) | 1981-06-17 |
| CA1107285A (en) | 1981-08-18 |
| US4142051A (en) | 1979-02-27 |
| DE2811847A1 (de) | 1979-09-20 |
| JPS5755716B2 (cs) | 1982-11-25 |
| DD141158A1 (de) | 1980-04-16 |
| AU521523B2 (en) | 1982-04-08 |
| HU179219B (en) | 1982-09-28 |
| ZA787312B (en) | 1979-12-27 |
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