CH620682A5 - Process for the preparation of novel 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts - Google Patents
Process for the preparation of novel 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts Download PDFInfo
- Publication number
- CH620682A5 CH620682A5 CH1267875A CH1267875A CH620682A5 CH 620682 A5 CH620682 A5 CH 620682A5 CH 1267875 A CH1267875 A CH 1267875A CH 1267875 A CH1267875 A CH 1267875A CH 620682 A5 CH620682 A5 CH 620682A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- chloro
- formula
- acid addition
- imidazolidine
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 150000003839 salts Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title 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 title description 4
- -1 2-ethyl-6-methylphenyl Chemical group 0.000 claims description 25
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 2
- UBEPBFYKYSULAI-UHFFFAOYSA-N 2-phenyl-2,5-dihydro-1H-imidazol-4-amine Chemical class N1C(=N)CNC1C1=CC=CC=C1 UBEPBFYKYSULAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 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 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 235000002639 sodium chloride Nutrition 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical class Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 description 4
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- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 239000008346 aqueous phase Substances 0.000 description 3
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- 239000003480 eluent Substances 0.000 description 3
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- GNYKPRZVSYJFIV-UHFFFAOYSA-N imidazolidin-1-ium;chloride Chemical compound Cl.C1CNCN1 GNYKPRZVSYJFIV-UHFFFAOYSA-N 0.000 description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
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- 230000001225 therapeutic effect Effects 0.000 description 3
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- KEYVECAMLDRXSJ-UHFFFAOYSA-N 2,6-bis(trifluoromethyl)aniline Chemical compound NC1=C(C(F)(F)F)C=CC=C1C(F)(F)F KEYVECAMLDRXSJ-UHFFFAOYSA-N 0.000 description 2
- BIMSFWCFKDVSNO-UHFFFAOYSA-N 2-bromo-6-chloroaniline Chemical compound NC1=C(Cl)C=CC=C1Br BIMSFWCFKDVSNO-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
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- 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
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- IUWWOCDHDVOZOJ-UHFFFAOYSA-N n-(2,6-difluorophenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound FC1=CC=CC(F)=C1N=C1NCCN1 IUWWOCDHDVOZOJ-UHFFFAOYSA-N 0.000 description 2
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- 239000011668 ascorbic acid Substances 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000011230 binding agent 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
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 238000004140 cleaning Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XKCNGNVSRKVSDD-UHFFFAOYSA-N ethane;phosphoric acid Chemical compound CC.OP(O)(O)=O XKCNGNVSRKVSDD-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- KRZGKJJPEOUIBI-UHFFFAOYSA-N hydron;thiourea;iodide Chemical compound I.NC(S)=N KRZGKJJPEOUIBI-UHFFFAOYSA-N 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 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
- 239000000463 material Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 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
- 239000012452 mother liquor Substances 0.000 description 1
- BMMCJVUOSITUBN-UHFFFAOYSA-N n-(2-bromo-6-chlorophenyl)-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Br)=C1N=C1NCCN1 BMMCJVUOSITUBN-UHFFFAOYSA-N 0.000 description 1
- NEHXUXBKAMVHSA-UHFFFAOYSA-N n-(2-chloro-6-fluorophenyl)-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.FC1=CC=CC(Cl)=C1N=C1NCCN1 NEHXUXBKAMVHSA-UHFFFAOYSA-N 0.000 description 1
- KPGWCJQEDRITON-UHFFFAOYSA-N n-(2-ethyl-6-methylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound CCC1=CC=CC(C)=C1NC1=NCCN1 KPGWCJQEDRITON-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 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
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 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
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2446758A DE2446758C3 (de) | 1974-10-01 | 1974-10-01 | 2-(2-Fluor-6-trifluormethylphenylimino)-imidazolidin, dessen Säureadditionssalze, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung bei der Bekämpfung der Hypertonie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH620682A5 true CH620682A5 (en) | 1980-12-15 |
Family
ID=5927202
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1267875A CH620682A5 (en) | 1974-10-01 | 1975-09-30 | Process for the preparation of novel 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
| CH506480A CH626352A5 (en) | 1974-10-01 | 1980-07-01 | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
| CH506280A CH627452A5 (en) | 1974-10-01 | 1980-07-01 | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
| CH506380A CH627453A5 (en) | 1974-10-01 | 1980-07-01 | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
| CH506580A CH627454A5 (en) | 1974-10-01 | 1980-07-01 | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH506480A CH626352A5 (en) | 1974-10-01 | 1980-07-01 | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
| CH506280A CH627452A5 (en) | 1974-10-01 | 1980-07-01 | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
| CH506380A CH627453A5 (en) | 1974-10-01 | 1980-07-01 | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
| CH506580A CH627454A5 (en) | 1974-10-01 | 1980-07-01 | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts |
Country Status (27)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE2806811A1 (de) * | 1978-02-17 | 1979-08-23 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylimino- imidazolidine, deren saeureadditionssalze, diese enthaltene arzneimittel und verfahren zur herstellung derselben |
| DE2806775A1 (de) * | 1978-02-17 | 1979-08-30 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylimino- imidazolidine deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben |
| ZA801680B (en) * | 1979-04-03 | 1981-03-25 | Fujisawa Pharmaceutical Co | 2-imidazoline derivatives,process for the preparation thereof and the pharmaceutical composition of the same |
| HU192986B (en) | 1984-05-23 | 1987-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of imidasodiline derivatives |
| AU2007213887A1 (en) * | 2006-01-27 | 2007-08-16 | F. Hoffmann-La Roche Ag | Use of 2-imidazoles for the treatment of CNS disorders |
| WO2008092785A1 (en) | 2007-02-02 | 2008-08-07 | F. Hoffmann-La Roche Ag | Novel 2-aminooxazolines as taar1 ligands for cns disorders |
| MX2009008465A (es) | 2007-02-15 | 2009-08-20 | Hoffmann La Roche | Nuevas 2-aminooxazolinas como ligandos de taar1. |
| US8242153B2 (en) | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| US8354441B2 (en) | 2009-11-11 | 2013-01-15 | Hoffmann-La Roche Inc. | Oxazoline derivatives |
| US9452980B2 (en) | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| PT3430010T (pt) | 2016-03-17 | 2020-09-10 | Hoffmann La Roche | Derivado de 5-etiol-4-metil-pirazol-3-carboxamida com atividade de agonista de taar |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3236857A (en) * | 1961-10-09 | 1966-02-22 | Boehringer Sohn Ingelheim | 2-(phenyl-amino)-1, 3-diazacyclopentene-(2) substitution products |
| DE1670807A1 (de) * | 1967-02-17 | 1971-03-11 | Bayer Ag | Verfahren zur Herstellung von cyclischen Guanidinen |
| DE1670918A1 (de) * | 1967-09-07 | 1971-04-08 | Bayer Ag | Verfahren zur Herstellung von 2-Aryl-amino-substituierten stickstoffhaltigen Heterocyclen |
| 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 |
-
1974
- 1974-10-01 DE DE2446758A patent/DE2446758C3/de not_active Expired
-
1975
- 1975-09-22 AT AT722875A patent/AT344159B/de not_active IP Right Cessation
- 1975-09-23 SU SU7502174605A patent/SU575026A3/ru active
- 1975-09-26 PH PH17613A patent/PH13653A/en unknown
- 1975-09-29 DD DD188613A patent/DD123602A5/xx unknown
- 1975-09-29 BG BG032014A patent/BG25221A3/xx unknown
- 1975-09-29 CS CS756573A patent/CS193524B2/cs unknown
- 1975-09-29 LU LU73472A patent/LU73472A1/xx unknown
- 1975-09-29 BG BG031110A patent/BG25220A3/xx unknown
- 1975-09-30 NZ NZ178810A patent/NZ178810A/xx unknown
- 1975-09-30 GB GB40012/75A patent/GB1515019A/en not_active Expired
- 1975-09-30 JP JP50118196A patent/JPS6018653B2/ja not_active Expired
- 1975-09-30 ZA ZA756185A patent/ZA756185B/xx unknown
- 1975-09-30 ES ES441385A patent/ES441385A1/es not_active Expired
- 1975-09-30 DK DK441875A patent/DK441875A/da not_active Application Discontinuation
- 1975-09-30 PL PL1975197816A patent/PL98984B1/pl unknown
- 1975-09-30 HU HU75BO1573A patent/HU178469B/hu unknown
- 1975-09-30 NO NO753314A patent/NO143459C/no unknown
- 1975-09-30 CH CH1267875A patent/CH620682A5/de not_active IP Right Cessation
- 1975-09-30 CA CA236,670A patent/CA1056836A/en not_active Expired
- 1975-09-30 PL PL1975183670A patent/PL97003B1/pl unknown
- 1975-09-30 BE BE160578A patent/BE834051A/xx not_active IP Right Cessation
- 1975-09-30 IL IL48214A patent/IL48214A/xx unknown
- 1975-09-30 FI FI752728A patent/FI61883C/fi not_active IP Right Cessation
- 1975-09-30 NL NL7511490A patent/NL7511490A/xx not_active Application Discontinuation
- 1975-10-01 FR FR7530117A patent/FR2286649A1/fr active Granted
- 1975-10-01 IE IE2150/75A patent/IE42130B1/en unknown
- 1975-10-01 SE SE7511028A patent/SE418497B/xx not_active IP Right Cessation
-
1976
- 1976-02-04 ES ES444901A patent/ES444901A1/es not_active Expired
- 1976-02-04 ES ES444900A patent/ES444900A1/es not_active Expired
- 1976-02-04 ES ES444898A patent/ES444898A1/es not_active Expired
-
1980
- 1980-07-01 CH CH506480A patent/CH626352A5/de not_active IP Right Cessation
- 1980-07-01 CH CH506280A patent/CH627452A5/de not_active IP Right Cessation
- 1980-07-01 CH CH506380A patent/CH627453A5/de not_active IP Right Cessation
- 1980-07-01 CH CH506580A patent/CH627454A5/de not_active IP Right Cessation
-
1981
- 1981-09-24 YU YU02302/81A patent/YU230281A/xx unknown
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Legal Events
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| PL | Patent ceased | ||
| PL | Patent ceased |