CA1112648A - 2-[3,4-disubstituted-phenylimino]-imidazolidines - Google Patents
2-[3,4-disubstituted-phenylimino]-imidazolidinesInfo
- Publication number
- CA1112648A CA1112648A CA342,041A CA342041A CA1112648A CA 1112648 A CA1112648 A CA 1112648A CA 342041 A CA342041 A CA 342041A CA 1112648 A CA1112648 A CA 1112648A
- Authority
- CA
- Canada
- Prior art keywords
- fluoro
- compound
- formula
- imidazolidine
- process according
- 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.)
- Expired
Links
- -1 2-[3,4-disubstituted-phenylimino]-imidazolidines Chemical class 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000002253 acid Substances 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims description 43
- 230000008569 process Effects 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- KJZXVFVJSRJASY-UHFFFAOYSA-N 1-[2-(4-fluoro-3-nitroanilino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1NC1=CC=C(F)C([N+]([O-])=O)=C1 KJZXVFVJSRJASY-UHFFFAOYSA-N 0.000 claims description 3
- HKWFCVUHNYCCNR-UHFFFAOYSA-N 1-n-(4,5-dihydro-1h-imidazol-2-yl)-4-fluorobenzene-1,3-diamine Chemical compound C1=C(F)C(N)=CC(N=C2NCCN2)=C1 HKWFCVUHNYCCNR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 claims description 2
- LLIOADBCFIXIEU-UHFFFAOYSA-N 4-fluoro-3-nitroaniline Chemical compound NC1=CC=C(F)C([N+]([O-])=O)=C1 LLIOADBCFIXIEU-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 239000011230 binding agent Substances 0.000 claims description 2
- 230000020176 deacylation Effects 0.000 claims description 2
- 238000005947 deacylation reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- TVOMVESJWMRWPR-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NCCN1 TVOMVESJWMRWPR-UHFFFAOYSA-N 0.000 claims description 2
- NZYMFXFUFFNQPM-UHFFFAOYSA-N n-(3-fluoro-4-methylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=C(F)C(C)=CC=C1NC1=NCCN1 NZYMFXFUFFNQPM-UHFFFAOYSA-N 0.000 claims description 2
- DVXHIWKNAKNGND-UHFFFAOYSA-N n-(4-fluoro-3-methylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=C(F)C(C)=CC(NC=2NCCN=2)=C1 DVXHIWKNAKNGND-UHFFFAOYSA-N 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- NHDLMBUAIWPQQA-UHFFFAOYSA-N n-(4-fluoro-3-nitrophenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=C(F)C([N+](=O)[O-])=CC(NC=2NCCN=2)=C1 NHDLMBUAIWPQQA-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 230000000850 deacetylating effect Effects 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- JJWACYUTERPMBM-UHFFFAOYSA-N 1-acetylimidazolidin-2-one Chemical compound CC(=O)N1CCNC1=O JJWACYUTERPMBM-UHFFFAOYSA-N 0.000 claims 1
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- BKWCAFAZEHXGPT-UHFFFAOYSA-N [I-].FC1=C(C=C(C=C1)[NH+]=C(SC)N)C Chemical compound [I-].FC1=C(C=C(C=C1)[NH+]=C(SC)N)C BKWCAFAZEHXGPT-UHFFFAOYSA-N 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 230000003518 presynaptic effect Effects 0.000 abstract description 3
- 208000019695 Migraine disease Diseases 0.000 abstract description 2
- 206010027599 migraine Diseases 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
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- 229960001866 silicon dioxide Drugs 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- BNJBUDJCJPWKRQ-UHFFFAOYSA-H dipotassium;hexaiodoplatinum(2-) Chemical compound [K+].[K+].[I-].[I-].[I-].[I-].[I-].[I-].[Pt+4] BNJBUDJCJPWKRQ-UHFFFAOYSA-H 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
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- 238000003828 vacuum filtration Methods 0.000 description 4
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 239000012153 distilled water Substances 0.000 description 3
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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
- 229920002261 Corn starch Polymers 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
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- 238000001556 precipitation Methods 0.000 description 2
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- 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 description 1
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- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 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
- 230000000630 rising effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 230000001515 vagal effect Effects 0.000 description 1
- 229940005605 valeric acid Drugs 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Luminescent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782854659 DE2854659A1 (de) | 1978-12-18 | 1978-12-18 | Neue 3,4-disubstituierte 2-phenylimino-imidazolidine, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| DEP2854659.0 | 1978-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1112648A true CA1112648A (en) | 1981-11-17 |
Family
ID=6057553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA342,041A Expired CA1112648A (en) | 1978-12-18 | 1979-12-17 | 2-[3,4-disubstituted-phenylimino]-imidazolidines |
Country Status (18)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6066740A (en) * | 1997-11-25 | 2000-05-23 | The Procter & Gamble Company | Process for making 2-amino-2-imidazoline, guanidine and 2-amino-3,4,5,6-tetrahydropyrimidine derivatives |
| US6316637B1 (en) | 1994-08-04 | 2001-11-13 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| US6495583B1 (en) | 1997-03-25 | 2002-12-17 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2933930A1 (de) * | 1979-08-22 | 1981-03-12 | C.H. Boehringer Sohn, 6507 Ingelheim | 2-(2-chlor-4-cyclopropyl-phenylimino)-imidazolidin, dessen saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben. |
| HU192986B (en) * | 1984-05-23 | 1987-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of imidasodiline derivatives |
| DE19514579A1 (de) | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
| CO4910165A1 (es) * | 1996-11-25 | 2000-04-24 | Procter & Gamble | Procedimiento para elaboracion de derivados de 2-amino-2- imidazolina, guanidina y 2-amino-3,4,5,6-tetrahidropirimidi- na |
| CN111303038A (zh) * | 2020-03-18 | 2020-06-19 | 滨州德润化工有限责任公司 | 一种油田水处理用缓蚀剂两性咪唑啉制作工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL123037C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-10-04 | |||
| SE331280B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1965-10-01 | 1970-12-21 | Boehringer Sohn Ingelheim | |
| DE1545628A1 (de) * | 1965-10-01 | 1970-06-25 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von blutdrucksenkend und sedativ wirksamen Derivaten des 2-(2-Halogenanilino)-1,3-diazacyclopentens-(2) |
| AT278775B (de) * | 1967-01-19 | 1970-02-10 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur Herstellung von Δ<2>-Imidazolinderivaten und ihren Salzen |
| AT330769B (de) * | 1974-04-05 | 1976-07-26 | Chemie Linz Ag | Verfahren zur herstellung von 2-arylamino- 2-imidazolin-derivaten und ihren salzen |
| 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 |
-
1978
- 1978-12-18 DE DE19782854659 patent/DE2854659A1/de not_active Withdrawn
-
1979
- 1979-11-08 AT AT79104381T patent/ATE1903T1/de not_active IP Right Cessation
- 1979-11-08 DE DE7979104381T patent/DE2964166D1/de not_active Expired
- 1979-11-08 EP EP79104381A patent/EP0012822B1/de not_active Expired
- 1979-11-28 GR GR60628A patent/GR73913B/el unknown
- 1979-12-13 PT PT70592A patent/PT70592A/pt unknown
- 1979-12-17 ES ES486971A patent/ES486971A0/es active Granted
- 1979-12-17 ES ES486970A patent/ES8102100A1/es not_active Expired
- 1979-12-17 YU YU3089/79A patent/YU41901B/xx unknown
- 1979-12-17 IE IE2447/79A patent/IE49239B1/en unknown
- 1979-12-17 JP JP16289679A patent/JPS5583754A/ja active Granted
- 1979-12-17 AU AU53893/79A patent/AU526539B2/en not_active Ceased
- 1979-12-17 FI FI793948A patent/FI68814C/fi not_active IP Right Cessation
- 1979-12-17 IL IL58971A patent/IL58971A/xx unknown
- 1979-12-17 ES ES486967A patent/ES8103054A1/es not_active Expired
- 1979-12-17 DK DK537179A patent/DK146821C/da not_active IP Right Cessation
- 1979-12-17 NZ NZ192426A patent/NZ192426A/en unknown
- 1979-12-17 NO NO794114A patent/NO148555C/no unknown
- 1979-12-17 CA CA342,041A patent/CA1112648A/en not_active Expired
- 1979-12-18 ZA ZA00796832A patent/ZA796832B/xx unknown
-
1983
- 1983-03-22 PH PH28680A patent/PH22130A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6316637B1 (en) | 1994-08-04 | 2001-11-13 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| US6403626B1 (en) | 1994-08-04 | 2002-06-11 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| US6436982B1 (en) | 1994-08-04 | 2002-08-20 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| US6495583B1 (en) | 1997-03-25 | 2002-12-17 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| US6066740A (en) * | 1997-11-25 | 2000-05-23 | The Procter & Gamble Company | Process for making 2-amino-2-imidazoline, guanidine and 2-amino-3,4,5,6-tetrahydropyrimidine derivatives |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |