SE440079B - Substituerade 5-(2-imidazolin-2-yl)-aminopyrimidiner och farmaceutisk komposition - Google Patents
Substituerade 5-(2-imidazolin-2-yl)-aminopyrimidiner och farmaceutisk kompositionInfo
- Publication number
- SE440079B SE440079B SE7909392A SE7909392A SE440079B SE 440079 B SE440079 B SE 440079B SE 7909392 A SE7909392 A SE 7909392A SE 7909392 A SE7909392 A SE 7909392A SE 440079 B SE440079 B SE 440079B
- Authority
- SE
- Sweden
- Prior art keywords
- imidazolin
- aminopyrimidine
- methyl
- carbon atoms
- blood pressure
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- -1 2-IMIDAZOLIN-2-YL Chemical class 0.000 title description 20
- 150000005005 aminopyrimidines Chemical class 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- OENDOJDJDYXZJR-UHFFFAOYSA-N 4-(4,5-dihydro-1H-imidazol-2-yl)pyrimidin-2-amine Chemical compound N1C(=NCC1)C1=NC(=NC=C1)N OENDOJDJDYXZJR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- OIARYBGUYNKKOW-UHFFFAOYSA-N 5-(4,5-dihydro-1h-imidazol-2-yl)pyrimidin-2-amine Chemical class C1=NC(N)=NC=C1C1=NCCN1 OIARYBGUYNKKOW-UHFFFAOYSA-N 0.000 claims 3
- 230000001384 anti-glaucoma Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
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- 230000036772 blood pressure Effects 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
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- 150000002367 halogens Chemical group 0.000 description 8
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- OEMPTJPXOCCVPP-UHFFFAOYSA-N 4-chloro-5-(4,5-dihydro-1h-imidazol-2-yl)-2-methyl-6-methylsulfanyl-2h-pyrimidin-1-amine Chemical compound ClC1=NC(C)N(N)C(SC)=C1C1=NCCN1 OEMPTJPXOCCVPP-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000002220 antihypertensive agent Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
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- 229940030600 antihypertensive agent Drugs 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- SFPCGPWJDDRSRL-UHFFFAOYSA-N 1-(4,5-dihydroimidazol-1-yl)ethanone Chemical class CC(=O)N1CCN=C1 SFPCGPWJDDRSRL-UHFFFAOYSA-N 0.000 description 4
- OAIPRQSPYGPMAG-UHFFFAOYSA-N 4,6-dichloro-2-cyclopropylpyrimidin-5-amine Chemical compound N1=C(Cl)C(N)=C(Cl)N=C1C1CC1 OAIPRQSPYGPMAG-UHFFFAOYSA-N 0.000 description 4
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- 229910052736 halogen Inorganic materials 0.000 description 4
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- 238000001990 intravenous administration Methods 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XCAAKLMJGXTCMA-UHFFFAOYSA-N 4,6-dichloro-2-cyclopropyl-5-nitropyrimidine Chemical compound N1=C(Cl)C([N+](=O)[O-])=C(Cl)N=C1C1CC1 XCAAKLMJGXTCMA-UHFFFAOYSA-N 0.000 description 3
- KATIQOPFTJLEKZ-UHFFFAOYSA-N 5-(4,5-dihydro-1h-imidazol-2-yl)-4-methoxy-2-methyl-6-methylsulfanyl-2h-pyrimidin-1-amine Chemical compound COC1=NC(C)N(N)C(SC)=C1C1=NCCN1 KATIQOPFTJLEKZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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- LODQXLJNUJXOHS-UHFFFAOYSA-N 2-cyclopropyl-4-hydroxy-5-nitro-1h-pyrimidin-6-one Chemical compound OC1=C([N+]([O-])=O)C(O)=NC(C2CC2)=N1 LODQXLJNUJXOHS-UHFFFAOYSA-N 0.000 description 2
- NMQWSFISZWSJDX-UHFFFAOYSA-N 4,6-dichloro-5-(4,5-dihydro-1h-imidazol-2-yl)pyrimidin-2-amine Chemical compound ClC1=NC(N)=NC(Cl)=C1C1=NCCN1 NMQWSFISZWSJDX-UHFFFAOYSA-N 0.000 description 2
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- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- IVZHAGHNBCEAIG-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-(4,6-diethoxypyrimidin-5-yl)azanium;iodide Chemical compound [I-].CCOC1=NC=NC(OCC)=C1[NH+]=C(N)SC IVZHAGHNBCEAIG-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 210000003703 cisterna magna Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- FXFPOKGPAPEJNE-UHFFFAOYSA-N cyclopropanecarboximidamide Chemical compound NC(=N)C1CC1 FXFPOKGPAPEJNE-UHFFFAOYSA-N 0.000 description 1
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- KRZGKJJPEOUIBI-UHFFFAOYSA-N hydron;thiourea;iodide Chemical compound I.NC(S)=N KRZGKJJPEOUIBI-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 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
- 238000005259 measurement Methods 0.000 description 1
- 210000001767 medulla oblongata Anatomy 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QHARUBGIFUCXIV-UHFFFAOYSA-N n-[(4,6-diethoxypyrimidin-5-yl)carbamothioyl]benzamide Chemical compound CCOC1=NC=NC(OCC)=C1NC(=S)NC(=O)C1=CC=CC=C1 QHARUBGIFUCXIV-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- INDZTCRIYSRWOH-UHFFFAOYSA-N undec-10-enyl carbamimidothioate;hydroiodide Chemical compound I.NC(=N)SCCCCCCCCCC=C INDZTCRIYSRWOH-UHFFFAOYSA-N 0.000 description 1
- 210000002385 vertebral artery Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2849537A DE2849537C2 (de) | 1978-11-15 | 1978-11-15 | Substituierte 5-(2-Imidazolin-2-yl)-aminopyrimidine, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| DE19792937023 DE2937023A1 (de) | 1979-09-13 | 1979-09-13 | Neue substituierte 5-(2-imidazolin-2-yl)-aminopyrimidine und verfahren zu deren herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7909392L SE7909392L (sv) | 1980-05-16 |
| SE440079B true SE440079B (sv) | 1985-07-15 |
Family
ID=25776489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7909392A SE440079B (sv) | 1978-11-15 | 1979-11-14 | Substituerade 5-(2-imidazolin-2-yl)-aminopyrimidiner och farmaceutisk komposition |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4323570A (nl) |
| AT (1) | AT374197B (nl) |
| AU (1) | AU541305B1 (nl) |
| CA (1) | CA1138454A (nl) |
| CH (1) | CH642965A5 (nl) |
| DK (1) | DK150142C (nl) |
| ES (1) | ES486349A1 (nl) |
| FR (1) | FR2441625A1 (nl) |
| GB (1) | GB2039275B (nl) |
| IT (1) | IT1127225B (nl) |
| NL (2) | NL190553C (nl) |
| SE (1) | SE440079B (nl) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2146986B (en) * | 1983-09-23 | 1987-06-17 | Lilly Co Eli | Process for preparing 5-substituted pyrimidines |
| DE3729299A1 (de) * | 1987-09-02 | 1989-03-23 | Beiersdorf Ag | Transdermales therapeutisches system |
| DE3739779A1 (de) * | 1987-11-24 | 1989-06-08 | Beiersdorf Ag | Pharmazeutische praeparate |
| DE3904795C2 (de) * | 1989-02-17 | 2000-10-12 | Lilly Pharma Produktion Gmbh & | Pharmazeutisches Präparat und dessen Verwendung |
| DE4423177A1 (de) * | 1994-07-01 | 1996-01-04 | Kali Chemie Pharma Gmbh | Antihyperglykämisch wirksame Arzneimittel |
| US5972948A (en) * | 1994-07-01 | 1999-10-26 | Solvay Pharmaceuticals Gmbh | Method of inhibiting hyperglycemia and pharmaceutical composition for use therein |
| US5977121A (en) * | 1995-02-28 | 1999-11-02 | Eli Lilly And Company | Use of moxonidine for the treatment of atherosclerosis |
| DE19514579A1 (de) * | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
| IL118544A (en) * | 1995-06-07 | 2001-08-08 | Smithkline Beecham Corp | History of imidazole, the process for their preparation and the pharmaceutical preparations containing them |
| CA2182851A1 (en) * | 1995-08-15 | 1997-02-16 | August Masaru Watanabe | Method for treating substance abuse withdrawal |
| HUP0003885A2 (hu) * | 1996-06-06 | 2001-04-28 | Eli Lilly And Co. | Készítmény pangásos szívelégtelenség kezelésére |
| ZA981029B (en) * | 1997-02-11 | 1999-08-10 | Lilly Co Eli | Pharmaceutical agents. |
| DE19722322A1 (de) * | 1997-05-28 | 1998-12-03 | Solvay Pharm Gmbh | Nephroprotektives Arzneimittel |
| CA2269971A1 (en) * | 1997-09-03 | 1999-03-11 | Trent Lee Abraham | Pyrimidine derivatives |
| DE19911371A1 (de) | 1999-03-15 | 2000-09-21 | Solvay Pharm Gmbh | Arzneimittel zur Behandlung von funktionellen Störungen und Erkrankungen der unteren Darmwege, insbesondere von damit einhergehenden abdominalen visceralen Schmerzen |
| PL372695A1 (en) * | 2002-06-19 | 2005-07-25 | Solvay Pharmaceuticals Gmbh | Medicament for the treatment of diseases requiring inhibition or a reduction in the activity of ph value-regulating bicarbonate transporter proteins |
| CA2637292A1 (en) * | 2006-01-27 | 2007-08-16 | F. Hoffmann-La Roche Ag | Use of 2-imidazoles for the treatment of cns disorders |
| ES2315967T3 (es) * | 2006-06-26 | 2009-04-01 | Chemagis Ltd. | Nuevo procedimiento de purificacion de moxonidina. |
| DE602006002738D1 (de) | 2006-06-26 | 2008-10-23 | Chemagis Ltd | Verbessertes Verfahren zur Herstellung von Moxonidine |
| EP1894926A1 (en) * | 2006-06-26 | 2008-03-05 | Chemagis Ltd. | Polymorphs of moxonidine and processes for preparation therefor |
| WO2008020425A1 (en) * | 2006-08-17 | 2008-02-21 | Chemagis Ltd. | Crystalline moxonidine comprising single tautomer and preparation process therefor |
| EP1894927B1 (en) * | 2006-08-31 | 2010-11-10 | Chemagis Ltd. | The use of moxonidine salts for purification of moxonidine |
| EP2076497B1 (en) * | 2006-10-19 | 2012-02-22 | F. Hoffmann-La Roche AG | Aminomethyl-4-imidazoles |
| DE602007005671D1 (de) * | 2006-10-19 | 2010-05-12 | Hoffmann La Roche | Aminomethyl-2-imidazole mit affinität zu mit dem trace-amin assoziierten rezeptoren |
| CN101535292A (zh) * | 2006-11-02 | 2009-09-16 | 弗·哈夫曼-拉罗切有限公司 | 作为痕量胺相关受体的调节剂的取代的2-咪唑类化合物 |
| AU2007321376A1 (en) * | 2006-11-16 | 2008-05-22 | F. Hoffmann-La Roche Ag | Substituted 4-imidazoles |
| WO2008073125A1 (en) * | 2006-12-12 | 2008-06-19 | Chemagis Ltd. | Moxonidine analogs, preparation processes and uses therefor |
| ES2364701T3 (es) * | 2006-12-13 | 2011-09-12 | F. Hoffmann-La Roche Ag | Nuevos 2-imidazoles como ligandos para receptores asociados a aminas trazas. |
| US20080146523A1 (en) * | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| AU2008209860A1 (en) * | 2007-02-02 | 2008-08-07 | F. Hoffmann-La Roche Ag | Novel 2-aminooxazolines as TAAR1 ligands for CNS disorders |
| KR101222412B1 (ko) * | 2007-02-15 | 2013-01-15 | 에프. 호프만-라 로슈 아게 | Ｔａａｒ1 리간드로서의 2-아미노옥사졸린 |
| CA2691082A1 (en) | 2007-07-02 | 2009-01-08 | F. Hoffmann-La Roche Ag | 2 -imidazolines having a good affinity to the trace amine associated receptors (taars) |
| KR101150628B1 (ko) * | 2007-07-03 | 2012-05-31 | 에프. 호프만-라 로슈 아게 | 4-이미다졸린 및 항우울제로서 이의 용도 |
| JP2010534701A (ja) * | 2007-07-27 | 2010-11-11 | エフ．ホフマン−ラ ロシュ アーゲー | Ｔａａｒリガンドとしての２−アゼチジンメタンアミン及び２−ピロリジンメタンアミン |
| EP2182935A1 (en) * | 2007-08-02 | 2010-05-12 | F. Hoffmann-Roche AG | The use of benzamide derivatives for the treatment of cns disorders |
| CA2695331A1 (en) * | 2007-08-03 | 2009-02-12 | F. Hoffmann-La Roche Ag | Pyridinecarboxamide and benzamide derivatives as taar1 ligands |
| MX2011000464A (es) * | 2008-07-24 | 2011-03-01 | Hoffmann La Roche | Derivados de 4,5-dihidro-oxazol-2-ilo. |
| US8242153B2 (en) * | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| US20100311798A1 (en) * | 2009-06-05 | 2010-12-09 | Decoret Guillaume | 2-aminooxazolines as taar1 ligands |
| 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 |
| EP2586779A1 (en) | 2011-10-24 | 2013-05-01 | Hetero Research Foundation | Process for the preparation of moxonidine |
| DE102012215896A1 (de) * | 2012-09-07 | 2014-03-13 | Wörwag Pharma GmbH & Co.KG | Moxonidinsynthese mit Hilfe organischer Basen |
| ES2608004T3 (es) | 2012-12-03 | 2017-04-05 | WÖRWAG PHARMA GmbH & Co. KG | Método mediante catálisis por transferencia de fase |
| EP2765131B1 (en) | 2013-02-08 | 2016-11-23 | Arevipharma GmbH | Process for the production of Moxonidine |
| EP2970214A1 (en) * | 2013-03-14 | 2016-01-20 | Farmak, A.S. | Improved process for the manufacture of moxonidine |
| EP2829540A1 (en) | 2013-07-26 | 2015-01-28 | Abbott Healthcare Products B.V. | Synthesis of substituted aminopyridines |
| KR102456567B1 (ko) | 2013-08-09 | 2022-10-19 | 알데릭스, 인코포레이티드 | 인산염 수송을 억제하기 위한 화합물 및 방법 |
| ES2819830T3 (es) | 2016-03-17 | 2021-04-19 | Hoffmann La Roche | Derivado de 5-etiol-4-metil-pirazol-3-carboxamida que tiene actividad como agonista de TAAR |
| US20240002369A1 (en) | 2020-11-12 | 2024-01-04 | 3Z Ehf | Novel treatments of attention deficit/hyperactivity disorder |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754832A (fr) | 1969-08-14 | 1971-02-15 | Beecham Group Ltd | Iminazolines |
| GB1319840A (en) * | 1970-08-27 | 1973-06-13 | Beecham Group Ltd | Substituted 5-amino imidazoles |
| BE795636A (fr) * | 1972-02-19 | 1973-08-20 | Schering Ag | Nitroimidazolylpyrimidines, et leur procede de preparation |
| US4029792A (en) * | 1972-02-29 | 1977-06-14 | Pfizer Inc. | (2-Imidazolin-2-ylamino) substituted -quinoxalines and -quinazolines as antihypertensive agents |
| DE2220906A1 (de) * | 1972-04-28 | 1973-11-15 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylaminoimidazoline-(2), deren saeureadditionssalze sowie verfahren zu deren herstellung |
| BE503170A (nl) * | 1975-09-02 |
-
1979
- 1979-11-07 US US06/092,134 patent/US4323570A/en not_active Expired - Lifetime
- 1979-11-08 NL NLAANVRAGE7908192,A patent/NL190553C/nl not_active IP Right Cessation
- 1979-11-14 GB GB7939460A patent/GB2039275B/en not_active Expired
- 1979-11-14 SE SE7909392A patent/SE440079B/sv not_active IP Right Cessation
- 1979-11-14 IT IT27284/79A patent/IT1127225B/it active
- 1979-11-14 CA CA000339844A patent/CA1138454A/en not_active Expired
- 1979-11-14 ES ES486349A patent/ES486349A1/es not_active Expired
- 1979-11-14 DK DK481879A patent/DK150142C/da not_active IP Right Cessation
- 1979-11-14 AT AT0727079A patent/AT374197B/de not_active IP Right Cessation
- 1979-11-15 AU AU52873/79A patent/AU541305B1/en not_active Expired
- 1979-11-15 FR FR7928169A patent/FR2441625A1/fr active Granted
- 1979-11-15 CH CH1021679A patent/CH642965A5/de not_active IP Right Cessation
-
1994
- 1994-06-27 NL NL940011C patent/NL940011I2/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL940011I1 (nl) | 1994-08-01 |
| ATA727079A (de) | 1983-08-15 |
| DK481879A (da) | 1980-05-16 |
| NL940011I2 (nl) | 1998-05-06 |
| NL7908192A (nl) | 1980-05-19 |
| NL190553C (nl) | 1994-04-18 |
| GB2039275A (en) | 1980-08-06 |
| NL190553B (nl) | 1993-11-16 |
| AT374197B (de) | 1984-03-26 |
| GB2039275B (en) | 1982-11-17 |
| FR2441625A1 (fr) | 1980-06-13 |
| DK150142B (da) | 1986-12-15 |
| CA1138454A (en) | 1982-12-28 |
| IT7927284A0 (it) | 1979-11-14 |
| DK150142C (da) | 1987-06-01 |
| IT1127225B (it) | 1986-05-21 |
| ES486349A1 (es) | 1980-06-16 |
| SE7909392L (sv) | 1980-05-16 |
| AU541305B1 (en) | 1985-01-03 |
| CH642965A5 (de) | 1984-05-15 |
| FR2441625B1 (nl) | 1981-12-31 |
| US4323570A (en) | 1982-04-06 |
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