FI69301C - Foerfarande foer framstaellning av terapeutiskt verksamma substituerade 2-fenyl-imino-imidazolidiner - Google Patents
Foerfarande foer framstaellning av terapeutiskt verksamma substituerade 2-fenyl-imino-imidazolidiner Download PDFInfo
- Publication number
- FI69301C FI69301C FI790510A FI790510A FI69301C FI 69301 C FI69301 C FI 69301C FI 790510 A FI790510 A FI 790510A FI 790510 A FI790510 A FI 790510A FI 69301 C FI69301 C FI 69301C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- formula
- preparation
- acid addition
- therapeutic
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- -1 3-bromo-4-fluorophenyl group Chemical group 0.000 claims description 4
- JCOPITWIWLFFPC-UHFFFAOYSA-N n-phenyl-4,5-dihydro-1h-imidazol-2-amine Chemical class N1CCN=C1NC1=CC=CC=C1 JCOPITWIWLFFPC-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 230000000052 comparative effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- OCBDFIRXBPZHLL-UHFFFAOYSA-N 2,6-dibromo-4-n-(4,5-dihydro-1h-imidazol-2-yl)benzene-1,4-diamine;hydrochloride Chemical compound Cl.C1=C(Br)C(N)=C(Br)C=C1N=C1NCCN1 OCBDFIRXBPZHLL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-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
- 241000282326 Felis catus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-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
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- JGBOUJCCXUEZPF-UHFFFAOYSA-N [K][I][Pt] Chemical compound [K][I][Pt] JGBOUJCCXUEZPF-UHFFFAOYSA-N 0.000 description 1
- OKPZIQOBDZDBRW-UHFFFAOYSA-N [Pt].[K] Chemical compound [Pt].[K] OKPZIQOBDZDBRW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000059 bradycardiac effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- IQXFQTQAXAPESE-UHFFFAOYSA-N imidazolidine;hydrobromide Chemical compound Br.C1CNCN1 IQXFQTQAXAPESE-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KFGKFKZXRFMBCP-UHFFFAOYSA-N n-(3-bromo-4-fluorophenyl)-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=C(Br)C(F)=CC=C1N=C1NCCN1 KFGKFKZXRFMBCP-UHFFFAOYSA-N 0.000 description 1
- IOUVWAKVDFTALH-UHFFFAOYSA-N n-(4-fluorophenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(F)=CC=C1NC1=NCCN1 IOUVWAKVDFTALH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2806775 | 1978-02-17 | ||
| DE19782806775 DE2806775A1 (de) | 1978-02-17 | 1978-02-17 | Neue substituierte 2-phenylimino- imidazolidine deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI790510A7 FI790510A7 (fi) | 1979-08-18 |
| FI69301B FI69301B (fi) | 1985-09-30 |
| FI69301C true FI69301C (fi) | 1986-01-10 |
Family
ID=6032231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI790510A FI69301C (fi) | 1978-02-17 | 1979-02-15 | Foerfarande foer framstaellning av terapeutiskt verksamma substituerade 2-fenyl-imino-imidazolidiner |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US4250186A (cs) |
| JP (1) | JPS54122273A (cs) |
| AT (1) | AT370093B (cs) |
| AU (1) | AU519356B2 (cs) |
| BE (1) | BE874252A (cs) |
| CA (1) | CA1115717A (cs) |
| CH (1) | CH640230A5 (cs) |
| CS (2) | CS207773B2 (cs) |
| DD (1) | DD142048A5 (cs) |
| DE (1) | DE2806775A1 (cs) |
| DK (1) | DK69479A (cs) |
| ES (2) | ES477784A1 (cs) |
| FI (1) | FI69301C (cs) |
| FR (1) | FR2417502A1 (cs) |
| GB (1) | GB2014575B (cs) |
| GR (2) | GR67626B (cs) |
| HU (1) | HU180430B (cs) |
| IE (1) | IE48073B1 (cs) |
| IL (1) | IL56678A (cs) |
| IT (1) | IT1113469B (cs) |
| LU (1) | LU80924A1 (cs) |
| NL (1) | NL7901241A (cs) |
| NO (1) | NO151239C (cs) |
| NZ (1) | NZ189684A (cs) |
| PH (1) | PH16188A (cs) |
| PL (2) | PL116527B1 (cs) |
| PT (1) | PT69239A (cs) |
| RO (2) | RO81504B (cs) |
| SE (1) | SE7901405L (cs) |
| SU (2) | SU812175A3 (cs) |
| YU (1) | YU36779A (cs) |
| ZA (1) | ZA79709B (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2854659A1 (de) * | 1978-12-18 | 1980-07-10 | Boehringer Sohn Ingelheim | Neue 3,4-disubstituierte 2-phenylimino-imidazolidine, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| DE3168754D1 (en) * | 1980-07-09 | 1985-03-21 | Beecham Group Plc | Clonidine derivatives useful in the treatment of diarrhoea |
| EP0070084A3 (en) * | 1981-04-24 | 1983-02-16 | Beecham Group Plc | Imidazoline derivatives |
| CA1201066A (en) * | 1981-11-20 | 1986-02-25 | Alcon Laboratories, Inc. | N-¬3,5-dichloro-4-(2-imidazolidinylideneamino)- phenyl|-acetamide solutions for lowering intraocular pressure |
| US4515800A (en) * | 1981-11-20 | 1985-05-07 | Icilio Cavero | Method of lowering intraocular pressure using phenylimino-imidazoles |
| US4644007A (en) * | 1981-11-20 | 1987-02-17 | Alcon Laboratories, Inc. | 3-chloro-4-(4,5-dihydro-1H-imidazo-2-yl)-amino-5-alkylbenzoic acids, esters, salts, compositions and methods |
| US4517199A (en) * | 1981-11-20 | 1985-05-14 | Alcon Laboratories, Inc. | Method for lowering intraocular pressure using phenylimino-imidazoles |
| US4461904A (en) * | 1981-11-20 | 1984-07-24 | Alcon Laboratories, Inc. | 2-(Trisubstituted phenylimino)-imidazolines |
| FR2521140A1 (fr) * | 1982-02-05 | 1983-08-12 | Synthelabo | Derives d'imidazolidine, leur preparation et leur application en therapeutique |
| GB2137191A (en) * | 1983-02-28 | 1984-10-03 | Sumitomo Chemical Co | Fungicidal N-phenylimidates |
| DE19514579A1 (de) * | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
| JP2003166617A (ja) | 2001-11-28 | 2003-06-13 | Honda Motor Co Ltd | トルクコンバータ付き内燃機関 |
| JP2007308392A (ja) * | 2006-05-16 | 2007-11-29 | Bayer Cropscience Ag | 殺虫性ベンズアミジン類 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899426A (en) * | 1959-08-11 | Synthesis of l | ||
| US2938038A (en) * | 1960-05-24 | X-dihydroxyphenylamino | ||
| FR1211341A (fr) * | 1955-12-19 | 1960-03-15 | A Wander Dr | Procédé pour la préparation de 2-amino-imidazolines |
| US3595961A (en) * | 1965-10-01 | 1971-07-27 | Boehringer Sohn Ingelheim | Hypotensive compositions containing 2-(2' - halo-anilino) - 1,3 -diazacyclopentenes-(2) and methods of using the same |
| DE1670274A1 (de) * | 1966-10-31 | 1970-07-16 | Boehringer Sohn Ingelheim | Neues Verfahren zur Herstellung von 2-Arylamino-1,3-diazacycloalkenen-(2) |
| AT285599B (de) * | 1968-06-21 | 1970-11-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen trisubstituierten 2-Arylaminoimidazolinen und ihren Salzen |
| DE2446758C3 (de) * | 1974-10-01 | 1979-01-04 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-(2-Fluor-6-trifluormethylphenylimino)-imidazolidin, dessen Säureadditionssalze, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung bei der Bekämpfung der Hypertonie |
| DE2523103C3 (de) * | 1975-05-24 | 1979-11-29 | C.H. Boehringer Sohn, 6507 Ingelheim | Substituierte 2-[N-Progargyl-N-(2-chlorphenyl)amino] -imidazoline-^), deren Säureadditionssalze, Verfahren zu ihrer Herstellung und deren Verwendung |
| DE2630060C2 (de) * | 1976-07-03 | 1984-04-19 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-(2-Brom-6-fluor-phenylimino)-imidazolidin, dessen Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung |
-
1978
- 1978-02-17 DE DE19782806775 patent/DE2806775A1/de not_active Withdrawn
-
1979
- 1979-02-09 SU SU792721602A patent/SU812175A3/ru active
- 1979-02-12 AT AT0101579A patent/AT370093B/de not_active IP Right Cessation
- 1979-02-12 GR GR58340A patent/GR67626B/el unknown
- 1979-02-13 RO RO103172A patent/RO81504B/ro unknown
- 1979-02-14 CH CH142879A patent/CH640230A5/de not_active IP Right Cessation
- 1979-02-15 FI FI790510A patent/FI69301C/fi not_active IP Right Cessation
- 1979-02-15 PT PT7969239A patent/PT69239A/pt unknown
- 1979-02-15 IL IL56678A patent/IL56678A/xx unknown
- 1979-02-15 HU HU79BO1764A patent/HU180430B/hu unknown
- 1979-02-15 YU YU00367/79A patent/YU36779A/xx unknown
- 1979-02-15 LU LU80924A patent/LU80924A1/de unknown
- 1979-02-15 DD DD79211044A patent/DD142048A5/de unknown
- 1979-02-15 IT IT48010/79A patent/IT1113469B/it active
- 1979-02-16 IE IE311/79A patent/IE48073B1/en unknown
- 1979-02-16 AU AU44325/79A patent/AU519356B2/en not_active Ceased
- 1979-02-16 BE BE0/193531A patent/BE874252A/xx not_active IP Right Cessation
- 1979-02-16 ES ES477784A patent/ES477784A1/es not_active Expired
- 1979-02-16 GB GB7905506A patent/GB2014575B/en not_active Expired
- 1979-02-16 ZA ZA79709A patent/ZA79709B/xx unknown
- 1979-02-16 NL NL7901241A patent/NL7901241A/xx not_active Application Discontinuation
- 1979-02-16 FR FR7904052A patent/FR2417502A1/fr active Granted
- 1979-02-16 CA CA321,805A patent/CA1115717A/en not_active Expired
- 1979-02-16 SE SE7901405A patent/SE7901405L/xx not_active Application Discontinuation
- 1979-02-16 NO NO790523A patent/NO151239C/no unknown
- 1979-02-16 JP JP1715679A patent/JPS54122273A/ja active Pending
- 1979-02-16 NZ NZ189684A patent/NZ189684A/xx unknown
- 1979-02-16 PL PL1979221508A patent/PL116527B1/pl unknown
- 1979-02-16 PL PL1979213475A patent/PL115759B1/pl unknown
- 1979-02-16 DK DK69479A patent/DK69479A/da not_active Application Discontinuation
- 1979-02-16 US US06/012,650 patent/US4250186A/en not_active Expired - Lifetime
- 1979-02-17 RO RO7996602A patent/RO76799A/ro unknown
- 1979-02-19 CS CS791092A patent/CS207773B2/cs unknown
- 1979-02-19 CS CS798500A patent/CS207774B2/cs unknown
- 1979-06-18 GR GR59371A patent/GR69232B/el unknown
- 1979-10-16 ES ES485043A patent/ES485043A1/es not_active Expired
-
1980
- 1980-01-30 SU SU802874805A patent/SU828964A3/ru active
- 1980-08-20 US US06/179,839 patent/US4293564A/en not_active Expired - Lifetime
- 1980-09-08 PH PH24546A patent/PH16188A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: C.H. BOEHRINGER SOHN |