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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- 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
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- 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
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- 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
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- 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 (de) |
| AT (1) | AT374197B (de) |
| AU (1) | AU541305B1 (de) |
| CA (1) | CA1138454A (de) |
| CH (1) | CH642965A5 (de) |
| DK (1) | DK150142C (de) |
| ES (1) | ES486349A1 (de) |
| FR (1) | FR2441625A1 (de) |
| GB (1) | GB2039275B (de) |
| IT (1) | IT1127225B (de) |
| NL (2) | NL190553C (de) |
| SE (1) | SE440079B (de) |
Families Citing this family (51)
| 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 |
| US5972948A (en) * | 1994-07-01 | 1999-10-26 | Solvay Pharmaceuticals Gmbh | Method of inhibiting hyperglycemia and pharmaceutical composition for use therein |
| DE4423177A1 (de) * | 1994-07-01 | 1996-01-04 | Kali Chemie Pharma Gmbh | Antihyperglykämisch wirksame Arzneimittel |
| 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 |
| CA2256720A1 (en) * | 1996-06-06 | 1997-12-11 | John Leeper Mcnay Jr. | Formulation and method for treating congestive heart failure |
| CA2229123A1 (en) * | 1997-02-11 | 1998-08-11 | Mitchell Irvin Steinberg | 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 |
| WO2004000312A2 (de) * | 2002-06-19 | 2003-12-31 | Solvay Pharmaceuticals Gmbh | Arzneimittel zur behandlung von eine inhibition oder aktivitätsverminderung von ph-wert-regulierenden bikarbonat-transporter-proteinen erfordernden erkrangungen |
| KR20080090546A (ko) * | 2006-01-27 | 2008-10-08 | 에프. 호프만-라 로슈 아게 | Ｃｎｓ 장애 치료용 2-이미다졸의 용도 |
| EP1894926A1 (de) * | 2006-06-26 | 2008-03-05 | Chemagis Ltd. | Polymorphe von Moxonidine und Verfahren zu deren Herstellung |
| ES2369113T3 (es) | 2006-06-26 | 2011-11-25 | Chemagis Ltd. | Procedimiento mejorado para producir moxonidina. |
| ES2315967T3 (es) * | 2006-06-26 | 2009-04-01 | Chemagis Ltd. | Nuevo procedimiento de purificacion de moxonidina. |
| WO2008020425A1 (en) * | 2006-08-17 | 2008-02-21 | Chemagis Ltd. | Crystalline moxonidine comprising single tautomer and preparation process therefor |
| ATE487712T1 (de) * | 2006-08-31 | 2010-11-15 | Chemagis Ltd | Verwendung der monoxidinssalze zur reinigung von monoxidin |
| WO2008046757A1 (en) * | 2006-10-19 | 2008-04-24 | 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 |
| KR101176700B1 (ko) * | 2006-11-02 | 2012-08-23 | 에프. 호프만-라 로슈 아게 | 미량 아민 결합된 수용체의 조절자로서 치환된 2-이미다졸 |
| JP2010510184A (ja) * | 2006-11-16 | 2010-04-02 | エフ．ホフマン−ラ ロシュ アーゲー | 置換４−イミダゾール類 |
| WO2008073125A1 (en) * | 2006-12-12 | 2008-06-19 | Chemagis Ltd. | Moxonidine analogs, preparation processes and uses therefor |
| AU2007332641A1 (en) * | 2006-12-13 | 2008-06-19 | F. Hoffmann-La Roche Ag | Novel 2 -imidazoles as ligands for trace amine associated receptors (TAAR) |
| US20080146523A1 (en) * | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| NZ578260A (en) * | 2007-02-02 | 2012-02-24 | Hoffmann La Roche | Novel 2-aminooxazolines as taar1 ligands for cns disorders |
| JP5130305B2 (ja) * | 2007-02-15 | 2013-01-30 | エフ．ホフマン−ラ ロシュ アーゲー | Ｔａａｒ１リガンドとしての２−アミノオキサゾリン |
| EP2173720A2 (de) | 2007-07-02 | 2010-04-14 | F. Hoffmann-Roche AG | 2-imidazoline mit guter affinität zu trace-amine-associated-rezeptoren (taars) |
| EP2173719A1 (de) * | 2007-07-03 | 2010-04-14 | F. Hoffmann-Roche AG | 4-imidazoline und ihre verwendung als antidepressiva |
| 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 |
| KR20100039429A (ko) * | 2007-08-02 | 2010-04-15 | 에프. 호프만-라 로슈 아게 | Ｃｎｓ 질환의 치료를 위한 벤즈아미드 유도체의 용도 |
| JP5341084B2 (ja) * | 2007-08-03 | 2013-11-13 | エフ．ホフマン−ラ ロシュ アーゲー | Ｔａａｒ１リガンドとしてのピリジンカルボキシアミド及びベンズアミド誘導体 |
| US8242153B2 (en) * | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| AU2009273324A1 (en) * | 2008-07-24 | 2010-01-28 | F. Hoffmann-La Roche Ag | 4,5-dihydro-oxazol-2-yl 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 (de) | 2011-10-24 | 2013-05-01 | Hetero Research Foundation | Verfahren zur Herstellung von 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 (de) | 2013-02-08 | 2016-11-23 | Arevipharma GmbH | Verfahren zur Herstellung von Moxonidin |
| WO2014140034A1 (en) * | 2013-03-14 | 2014-09-18 | Farmak, A.S. | Improved process for the manufacture of moxonidine |
| EP2829540A1 (de) | 2013-07-26 | 2015-01-28 | Abbott Healthcare Products B.V. | Synthese von substituierten Aminopyridinen |
| AU2014305843B2 (en) | 2013-08-09 | 2019-08-29 | Ardelyx, Inc. | Compounds and methods for inhibiting phosphate transport |
| JP6814814B2 (ja) | 2016-03-17 | 2021-01-20 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｔａａｒのアゴニストとしての活性を有する５−エチル−４−メチル−ピラゾール−３−カルボキサミド誘導体 |
| GB202103400D0 (en) * | 2021-03-11 | 2021-04-28 | 3Z Ehf | Novel treatments |
| 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 (de) * | 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/xx not_active IP Right Cessation
- 1979-11-14 IT IT27284/79A patent/IT1127225B/it active
- 1979-11-14 GB GB7939460A patent/GB2039275B/en not_active Expired
- 1979-11-14 AT AT0727079A patent/AT374197B/de not_active IP Right Cessation
- 1979-11-14 DK DK481879A patent/DK150142C/da not_active IP Right Cessation
- 1979-11-14 SE SE7909392A patent/SE440079B/sv not_active IP Right Cessation
- 1979-11-14 ES ES486349A patent/ES486349A1/es not_active Expired
- 1979-11-14 CA CA000339844A patent/CA1138454A/en not_active Expired
- 1979-11-15 CH CH1021679A patent/CH642965A5/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
-
1994
- 1994-06-27 NL NL940011C patent/NL940011I2/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2039275A (en) | 1980-08-06 |
| FR2441625A1 (fr) | 1980-06-13 |
| CH642965A5 (de) | 1984-05-15 |
| SE7909392L (sv) | 1980-05-16 |
| NL940011I2 (nl) | 1998-05-06 |
| NL7908192A (nl) | 1980-05-19 |
| NL190553B (nl) | 1993-11-16 |
| AT374197B (de) | 1984-03-26 |
| IT7927284A0 (it) | 1979-11-14 |
| DK150142B (da) | 1986-12-15 |
| US4323570A (en) | 1982-04-06 |
| DK481879A (da) | 1980-05-16 |
| ATA727079A (de) | 1983-08-15 |
| DK150142C (da) | 1987-06-01 |
| NL190553C (nl) | 1994-04-18 |
| AU541305B1 (en) | 1985-01-03 |
| CA1138454A (en) | 1982-12-28 |
| GB2039275B (en) | 1982-11-17 |
| IT1127225B (it) | 1986-05-21 |
| FR2441625B1 (de) | 1981-12-31 |
| ES486349A1 (es) | 1980-06-16 |
| NL940011I1 (nl) | 1994-08-01 |
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