DE2309160A1 - 2-imidazolin-2-yl-amino-substituierte, benzokondensierte, heterocyclische verbindungen und arzneipraeparate - Google Patents
2-imidazolin-2-yl-amino-substituierte, benzokondensierte, heterocyclische verbindungen und arzneipraeparateInfo
- Publication number
- DE2309160A1 DE2309160A1 DE19732309160 DE2309160A DE2309160A1 DE 2309160 A1 DE2309160 A1 DE 2309160A1 DE 19732309160 DE19732309160 DE 19732309160 DE 2309160 A DE2309160 A DE 2309160A DE 2309160 A1 DE2309160 A1 DE 2309160A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- imidazolin
- quinoxaline
- quinoline
- compounds
- 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.)
- Pending
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 45
- -1 2-imidazolin-2-yl-amino group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 18
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical group N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- XYLJNLCSTIOKRM-UHFFFAOYSA-N Alphagan Chemical compound C1=CC2=NC=CN=C2C(Br)=C1NC1=NCCN1 XYLJNLCSTIOKRM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 2
- MBIGYTUJAQEBHM-UHFFFAOYSA-N 5-bromo-n-(4,5-dihydro-1h-imidazol-2-yl)quinolin-6-amine Chemical compound C1=CC2=NC=CC=C2C(Br)=C1NC1=NCCN1 MBIGYTUJAQEBHM-UHFFFAOYSA-N 0.000 claims 1
- AHRAZMOUGNXADW-UHFFFAOYSA-N 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)quinolin-6-amine Chemical compound C1=CC2=NC=CC=C2C(Cl)=C1NC1=NCCN1 AHRAZMOUGNXADW-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
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- 150000002540 isothiocyanates Chemical class 0.000 description 8
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 7
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(II) oxide Inorganic materials [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003246 quinazolines Chemical class 0.000 description 3
- 150000003252 quinoxalines Chemical class 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- YKGMGCYABGHZRB-UHFFFAOYSA-N 5-bromoquinoxalin-6-amine;hydrobromide Chemical compound Br.N1=CC=NC2=C(Br)C(N)=CC=C21 YKGMGCYABGHZRB-UHFFFAOYSA-N 0.000 description 2
- JQVKAIMULVFQKM-UHFFFAOYSA-N 8-bromo-6-methylquinolin-5-amine;hydrobromide Chemical compound Br.N1=CC=CC2=C(N)C(C)=CC(Br)=C21 JQVKAIMULVFQKM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229940058934 aminoquinoline antimalarials Drugs 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- MSGRFBKVMUKEGZ-UHFFFAOYSA-N quinoxalin-6-amine Chemical compound N1=CC=NC2=CC(N)=CC=C21 MSGRFBKVMUKEGZ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UDAIGHZFMLGNDQ-UHFFFAOYSA-N 2-nitroquinoline Chemical class C1=CC=CC2=NC([N+](=O)[O-])=CC=C21 UDAIGHZFMLGNDQ-UHFFFAOYSA-N 0.000 description 1
- RLAIFIDRVAAEBW-UHFFFAOYSA-N 3-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C(Br)=C1 RLAIFIDRVAAEBW-UHFFFAOYSA-N 0.000 description 1
- MKGCGXTYVJCXAT-UHFFFAOYSA-N 5,7-dichloroquinolin-8-amine Chemical compound C1=CN=C2C(N)=C(Cl)C=C(Cl)C2=C1 MKGCGXTYVJCXAT-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- VJQWCCBDYLTRPZ-UHFFFAOYSA-N 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)quinoxalin-6-amine Chemical compound C1=CC2=NC=CN=C2C(Cl)=C1NC1=NCCN1 VJQWCCBDYLTRPZ-UHFFFAOYSA-N 0.000 description 1
- ZWMOGBQIIIKCLO-UHFFFAOYSA-N 5-chloroquinoxalin-6-amine Chemical compound N1=CC=NC2=C(Cl)C(N)=CC=C21 ZWMOGBQIIIKCLO-UHFFFAOYSA-N 0.000 description 1
- XRRXXLJYPHYOLT-UHFFFAOYSA-N 6-chloro-8-methylquinolin-5-amine Chemical compound C1=CN=C2C(C)=CC(Cl)=C(N)C2=C1 XRRXXLJYPHYOLT-UHFFFAOYSA-N 0.000 description 1
- KQIDQFHIEFDWPM-UHFFFAOYSA-N 6-methylquinolin-5-amine Chemical compound N1=CC=CC2=C(N)C(C)=CC=C21 KQIDQFHIEFDWPM-UHFFFAOYSA-N 0.000 description 1
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- YYTGOWDNUUXBGS-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-5-iodoquinoxalin-6-amine Chemical compound C1=CC2=NC=CN=C2C(I)=C1NC1=NCCN1 YYTGOWDNUUXBGS-UHFFFAOYSA-N 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919672A GB1381979A (en) | 1972-02-29 | 1972-02-29 | Amino derivatives of quinoline quinoxaline and quinazoline |
| GB5162972 | 1972-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2309160A1 true DE2309160A1 (de) | 1973-09-27 |
Family
ID=26242776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732309160 Pending DE2309160A1 (de) | 1972-02-29 | 1973-02-23 | 2-imidazolin-2-yl-amino-substituierte, benzokondensierte, heterocyclische verbindungen und arzneipraeparate |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3890319A (enExample) |
| JP (2) | JPS5754516B2 (enExample) |
| AR (1) | AR213705A1 (enExample) |
| AU (1) | AU471598B2 (enExample) |
| BE (1) | BE795970A (enExample) |
| CA (1) | CA981678A (enExample) |
| CH (2) | CH576975A5 (enExample) |
| DE (1) | DE2309160A1 (enExample) |
| ES (2) | ES411804A1 (enExample) |
| FI (1) | FI63757C (enExample) |
| FR (1) | FR2181776B1 (enExample) |
| GB (1) | GB1381979A (enExample) |
| IE (1) | IE37519B1 (enExample) |
| MX (1) | MX3042E (enExample) |
| NL (1) | NL159102B (enExample) |
| SE (1) | SE417204B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2449087A2 (fr) * | 1979-02-16 | 1980-09-12 | Rhone Poulenc Ind | Nouveaux derives de l'isoquinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent |
| EP0426390A3 (en) * | 1989-10-31 | 1992-03-04 | Allergan, Inc. | Method for using (2-imidazolin-2-ylamino) quinoxalines to reduce or maintain intraocular pressure |
| WO1995010280A1 (en) * | 1993-10-13 | 1995-04-20 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US6323204B1 (en) | 1993-10-13 | 2001-11-27 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1463520A (en) * | 1974-09-06 | 1977-02-02 | Pfizer Ltd | Process for the production of imidazolines |
| JPS5373571A (en) * | 1976-12-10 | 1978-06-30 | Otsuka Pharmaceut Co Ltd | Carbostyril derivatives |
| JPS542338A (en) | 1977-04-22 | 1979-01-09 | Sandoz Ag | Pharmaceutical composition |
| US4188393A (en) | 1977-04-22 | 1980-02-12 | Sandoz Ltd. | Treating spastic conditions or relaxing muscles |
| US4486432A (en) * | 1982-09-30 | 1984-12-04 | Eli Lilly And Company | Quinoxalinedione leukotriene release inhibitors |
| FR2541680B1 (fr) * | 1983-02-24 | 1985-06-14 | Rhone Poulenc Sante | Nouveaux derives de l'amino-5 dithiole-1,2 one-3, leur preparation et les compositions medicinales qui les contiennent |
| JPS6118950U (ja) * | 1984-07-10 | 1986-02-03 | 財団法人鉄道総合技術研究所 | トロリ線の給油装置 |
| GB8827820D0 (en) * | 1988-11-29 | 1988-12-29 | Janssen Pharmaceutica Nv | (1h-azol-1-ylmethyl)substituted quinoline derivatives |
| US5180721A (en) * | 1989-05-22 | 1993-01-19 | Allergan, Inc. | Combinations of selective alpha-adrenergic agonists and antagonists useful in lowering intraocular pressure |
| US5281591A (en) * | 1989-05-22 | 1994-01-25 | Allergan, Inc. | Combinations of selective alpha-adrenergic agonists and antagonists useful in lowering intraocular pressure |
| US5198442A (en) * | 1989-10-12 | 1993-03-30 | Allergan, Inc. | (2-imidazolin-2-ylamino) quinoxaline derivatives and methods for using same |
| US5231096A (en) * | 1989-10-12 | 1993-07-27 | Allergan, Inc. | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US5112822A (en) * | 1989-10-12 | 1992-05-12 | Allergan, Inc. | (2-imidazolin-2-ylamino) quinoxaline derivatives and methods for using same |
| US5326763A (en) * | 1989-10-12 | 1994-07-05 | Allergan, Inc. | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US5077292A (en) * | 1989-10-12 | 1991-12-31 | Allergan, Inc. | (2-imidazolin-2-ylamino) tetrahydroquinoxalines and methods for using same |
| US5204347A (en) * | 1989-10-12 | 1993-04-20 | Allergan, Inc. | Methods for using (2-imidazolin-2-ylamino) tetrahydroquinoxalines |
| US5215991A (en) * | 1990-01-26 | 1993-06-01 | Allergan, Inc. | Combination of selective alpha-adrenergic agonists and Na+ /H+ ex |
| US5130441A (en) * | 1990-02-06 | 1992-07-14 | Allergan, Inc. | Method for producing amino-2-imidazoline derivatives |
| US5237072A (en) * | 1990-02-06 | 1993-08-17 | Allergan, Inc. | Method for producing amino-2-imidazoline derivatives |
| US5252595A (en) * | 1990-02-28 | 1993-10-12 | Allergan, Inc. | Method for reducing or maintaining intraocular pressure in the mammalian eye by administering pharmaceutical compositions containing 2-(2-alkylphenylamino)-oxazolines, 2-(2-alkylphenylamino)-thiazolines and 2-(2-alkylphenylamino)-imidazolines |
| US5091528A (en) * | 1990-09-12 | 1992-02-25 | Allergan, Inc. | 6- or 7- (2-imino-2-imidazolidine)-1,4-benzoxazines as α adrenergic agents |
| US5580892A (en) * | 1993-10-22 | 1996-12-03 | Allergan | Method for using 2-(2-alkylphenylamino)-oxazolines as adrenergic agents |
| US5578607A (en) * | 1993-12-17 | 1996-11-26 | The Procter & Gamble Company | 6-(2-imidazolinylamino)quinoline compounds useful as alpha-2 adrenoceptor agonists |
| PT736020E (pt) * | 1993-12-17 | 2000-10-31 | Procter & Gamble | Compostos 6-(2-imidazolinilamino)quinolina uteis como alfa-2 adrenoceptor agonistas |
| US5576437A (en) * | 1993-12-17 | 1996-11-19 | The Procter & Gamble Company | 7-(2-imidazolnylamino) quinoline compounds useful as alpha-2 adrenoceptor agonists |
| CN1137755A (zh) * | 1993-12-17 | 1996-12-11 | 普罗克特和甘保尔公司 | 用作α-2肾上腺素能受体兴奋剂的6-(2-咪唑啉基氨基)喹喔啉化合物 |
| US5478858A (en) * | 1993-12-17 | 1995-12-26 | The Procter & Gamble Company | 5-(2-imidazolinylamino) benzimidazole compounds useful as alpha-2 adrenoceptor agonists |
| CA2158763C (en) * | 1994-02-08 | 2002-10-29 | David R. Pierce | Novel process for preparation of clonidine derivatives |
| EP0775134A4 (en) | 1994-08-04 | 1997-08-13 | Synaptic Pharma Corp | NEW BENZIMIDAZOLE DERIVATIVES |
| US6294563B1 (en) | 1994-10-27 | 2001-09-25 | Allergan Sales, Inc. | Combinations of prostaglandins and brimonidine or derivatives thereof |
| US6194415B1 (en) * | 1995-06-28 | 2001-02-27 | Allergan Sales, Inc. | Method of using (2-imidazolin-2-ylamino) quinoxoalines in treating neural injury |
| US5916900A (en) | 1995-06-29 | 1999-06-29 | The Procter & Gamble Company | 7-(2-imidazolinylamino)quinoline compounds useful as alpha-2 adrenoceptor agonists |
| ID22812A (id) * | 1996-11-25 | 1999-12-09 | Procter & Gamble | Senyawa 2-imidazolinilaminoindol yang berguna sebagai agonis adrenoseptor alfa-2 |
| US6172095B1 (en) | 1996-11-25 | 2001-01-09 | The Procter & Gamble Company | Guanidinylamino heterocycle compounds useful as alpha-2 adrenoceptor agonists |
| WO1998023612A1 (en) * | 1996-11-25 | 1998-06-04 | The Procter & Gamble Company | 2-imidazolinylaminobenzothiazole compounds useful as alpha-2 adrenoceptor agonists |
| US6306877B1 (en) | 1999-08-09 | 2001-10-23 | The Procter & Gamble Co. | Guanidinylamino heterocycle compounds useful as alpha-2 adrenoceptor agonists |
| KR20000069128A (ko) * | 1996-11-25 | 2000-11-25 | 데이비드 엠 모이어 | 알파-2 아드레날린수용체 아고니스트로서 유용한 2-이미다졸리닐아미노벤즈옥사졸 화합물 |
| AU730369B2 (en) | 1996-11-25 | 2001-03-08 | Board Of Regents Of The University Of Nebraska, The | Guanidinyl heterocycle compounds useful as alpha-2 adrenoceptor agonists |
| US6495583B1 (en) | 1997-03-25 | 2002-12-17 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| ES2223143T3 (es) | 1997-11-24 | 2005-02-16 | THE PROCTER & GAMBLE COMPANY | Derivados de 5-(2-imidazolinilamino)-bencimidazol, preparacion y uso de los mismos como agonistas de adrenorreceptores alfa con estabilidad metabolica mejorada. |
| WO2004073708A1 (en) | 1998-12-17 | 2004-09-02 | Dean Thomas R | Brinzolamide and brimonidine for treating ocular conditions |
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| DE10161767A1 (de) * | 2001-12-15 | 2003-06-26 | Merck Patent Gmbh | 2-Guanidino-4-heterocyclyl-chinazoline |
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| KR20130041803A (ko) | 2010-04-07 | 2013-04-25 | 알러간, 인코포레이티드 | 안과 조성물을 위한 보존제의 조합 |
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| US8053427B1 (en) | 2010-10-21 | 2011-11-08 | Galderma R&D SNC | Brimonidine gel composition |
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| GR1009419B (el) | 2017-11-07 | 2018-12-14 | Φαρματεν Αβεε | Οφθαλμικο φαρμακευτικο σκευασμα που περιεχει εναν συνδυασμο βρινζολαμιδης και βριμονιδινης και μεθοδος για την παρασκευη αυτου |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3560501A (en) * | 1966-09-15 | 1971-02-02 | Ciba Geigy Corp | Process for making dihydroquinazolines |
| US3594380A (en) * | 1969-02-18 | 1971-07-20 | American Home Prod | Isoquinolin-1(2h)-ones |
| BE766039A (fr) * | 1971-04-21 | 1971-09-16 | Labofina Sa | Nouveaux polymeres contenant des unites de pyrazole et procede de preparation de ces polymeres. |
-
0
- BE BE795970D patent/BE795970A/xx not_active IP Right Cessation
-
1972
- 1972-02-29 GB GB919672A patent/GB1381979A/en not_active Expired
-
1973
- 1973-02-08 AU AU51985/73A patent/AU471598B2/en not_active Expired
- 1973-02-13 SE SE7302024A patent/SE417204B/xx unknown
- 1973-02-14 IE IE236/73A patent/IE37519B1/xx unknown
- 1973-02-14 US US332485A patent/US3890319A/en not_active Expired - Lifetime
- 1973-02-14 FI FI436/73A patent/FI63757C/fi active
- 1973-02-15 MX MX129473U patent/MX3042E/es unknown
- 1973-02-20 ES ES411804A patent/ES411804A1/es not_active Expired
- 1973-02-21 JP JP48020280A patent/JPS5754516B2/ja not_active Expired
- 1973-02-22 CA CA164,361A patent/CA981678A/en not_active Expired
- 1973-02-23 DE DE19732309160 patent/DE2309160A1/de active Pending
- 1973-02-23 AR AR246774A patent/AR213705A1/es active
- 1973-02-27 ES ES412102A patent/ES412102A1/es not_active Expired
- 1973-02-28 CH CH293873A patent/CH576975A5/xx not_active IP Right Cessation
- 1973-02-28 FR FR7307157A patent/FR2181776B1/fr not_active Expired
- 1973-02-28 CH CH149075A patent/CH577500A5/xx not_active IP Right Cessation
- 1973-02-28 NL NL7302799.A patent/NL159102B/xx not_active IP Right Cessation
-
1980
- 1980-07-11 JP JP9493480A patent/JPS5625176A/ja active Granted
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2449087A2 (fr) * | 1979-02-16 | 1980-09-12 | Rhone Poulenc Ind | Nouveaux derives de l'isoquinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent |
| EP0426390A3 (en) * | 1989-10-31 | 1992-03-04 | Allergan, Inc. | Method for using (2-imidazolin-2-ylamino) quinoxalines to reduce or maintain intraocular pressure |
| WO1995010280A1 (en) * | 1993-10-13 | 1995-04-20 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US5552403A (en) * | 1993-10-13 | 1996-09-03 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US5561132A (en) * | 1993-10-13 | 1996-10-01 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US5587376A (en) * | 1993-10-13 | 1996-12-24 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US5703077A (en) * | 1993-10-13 | 1997-12-30 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US5714486A (en) * | 1993-10-13 | 1998-02-03 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US5773440A (en) * | 1993-10-13 | 1998-06-30 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
| US6323204B1 (en) | 1993-10-13 | 2001-11-27 | Allergan | Methods for using (2-imidazolin-2-ylamino) quinoxaline derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| IE37519B1 (en) | 1977-08-17 |
| NL7302799A (enExample) | 1973-08-31 |
| FI63757C (fi) | 1983-08-10 |
| JPS5625176A (en) | 1981-03-10 |
| AU5198573A (en) | 1974-08-08 |
| FI63757B (fi) | 1983-04-29 |
| CH576975A5 (enExample) | 1976-06-30 |
| SE417204B (sv) | 1981-03-02 |
| US3890319A (en) | 1975-06-17 |
| CH577500A5 (enExample) | 1976-07-15 |
| ES411804A1 (es) | 1976-05-01 |
| JPS5754516B2 (enExample) | 1982-11-18 |
| CA981678A (en) | 1976-01-13 |
| IE37519L (en) | 1973-08-29 |
| MX3042E (es) | 1980-03-04 |
| FR2181776B1 (enExample) | 1976-08-13 |
| ES412102A1 (es) | 1976-05-16 |
| GB1381979A (en) | 1975-01-29 |
| AU471598B2 (en) | 1976-04-29 |
| JPS4897878A (enExample) | 1973-12-13 |
| BE795970A (fr) | 1973-08-27 |
| JPS5745439B2 (enExample) | 1982-09-28 |
| AR213705A1 (es) | 1979-03-15 |
| FR2181776A1 (enExample) | 1973-12-07 |
| NL159102B (nl) | 1979-01-15 |
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