SE440079B - Substituerade 5-(2-imidazolin-2-yl)-aminopyrimidiner och farmaceutisk komposition - Google Patents

Substituerade 5-(2-imidazolin-2-yl)-aminopyrimidiner och farmaceutisk komposition

Info

Publication number: SE440079B
Authority: SE; Sweden
Prior art keywords: imidazolin; aminopyrimidine; methyl; carbon atoms; blood pressure
Prior art date: 1978-11-15

Application number

SE7909392A

Other languages

English (en)

Swedish (sv)

Other versions

SE7909392L (sv

Inventor

W Stenzel

E Cohnen

W Fleck

B Armah

Original Assignee

Beiersdorf Ag

Priority date (The priority date 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 date listed.)

1978-11-15

Filing date

1979-11-14

Publication date

1985-07-15

1978-11-15 Priority claimed from DE2849537A external-priority patent/DE2849537C2/de

1979-09-13 Priority claimed from DE19792937023 external-priority patent/DE2937023A1/de

1979-11-14 Application filed by Beiersdorf Ag filed Critical Beiersdorf Ag

1980-05-16 Publication of SE7909392L publication Critical patent/SE7909392L/xx

1985-07-15 Publication of SE440079B publication Critical patent/SE440079B/sv

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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
229960001701 chloroform Drugs 0.000 description 19
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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
230000004531 blood pressure lowering effect Effects 0.000 description 8
150000002367 halogens Chemical group 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
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101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 6
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CMSOCLHYOTXEHM-UHFFFAOYSA-N 1-[2-(1-amino-4,6-dichloro-2-methyl-2h-pyrimidin-5-yl)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound NN1C(C)N=C(Cl)C(C=2N(CCN=2)C(C)=O)=C1Cl CMSOCLHYOTXEHM-UHFFFAOYSA-N 0.000 description 5
241000282326 Felis catus Species 0.000 description 5
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229940030600 antihypertensive agent Drugs 0.000 description 5
230000004872 arterial blood pressure Effects 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
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238000000034 method Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 5
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
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000009530 blood pressure measurement Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000001704 evaporation Methods 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
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
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
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FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
125000000714 pyrimidinyl group Chemical group 0.000 description 3
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125000001424 substituent group Chemical group 0.000 description 3
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KVMGOOSNGQIZCT-UHFFFAOYSA-N 1-[2-(2-amino-4,6-dichloropyrimidin-5-yl)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1C1=C(Cl)N=C(N)N=C1Cl KVMGOOSNGQIZCT-UHFFFAOYSA-N 0.000 description 2
VFGWJXCRWXZRHV-UHFFFAOYSA-N 2-cyclopropyl-4-hydroxy-1h-pyrimidin-6-one Chemical compound OC1=CC(O)=NC(C2CC2)=N1 VFGWJXCRWXZRHV-UHFFFAOYSA-N 0.000 description 2
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
ZJEGAEBMGRVMJD-UHFFFAOYSA-N 5-(4,5-dihydro-1h-imidazol-2-yl)-2,6-dimethoxypyrimidin-4-amine Chemical compound COC1=NC(OC)=NC(N)=C1C1=NCCN1 ZJEGAEBMGRVMJD-UHFFFAOYSA-N 0.000 description 2
KIYAEOJQEWJGSY-UHFFFAOYSA-N 5-(4,5-dihydro-1h-imidazol-2-yl)-2-methyl-4,6-bis(methylsulfanyl)-2h-pyrimidin-1-amine Chemical compound CSC1=NC(C)N(N)C(SC)=C1C1=NCCN1 KIYAEOJQEWJGSY-UHFFFAOYSA-N 0.000 description 2
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150000005008 5-aminopyrimidines Chemical class 0.000 description 2
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UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
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CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SE7909392A 1978-11-15 1979-11-14 Substituerade 5-(2-imidazolin-2-yl)-aminopyrimidiner och farmaceutisk komposition SE440079B (sv)

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 (it)
AT (1)	AT374197B (it)
AU (1)	AU541305B1 (it)
CA (1)	CA1138454A (it)
CH (1)	CH642965A5 (it)
DK (1)	DK150142C (it)
ES (1)	ES486349A1 (it)
FR (1)	FR2441625A1 (it)
GB (1)	GB2039275B (it)
IT (1)	IT1127225B (it)
NL (2)	NL190553C (it)
SE (1)	SE440079B (it)

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US5972948A (en) *	1994-07-01	1999-10-26	Solvay Pharmaceuticals Gmbh	Method of inhibiting hyperglycemia and pharmaceutical composition for use therein
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IL123232A0 (en) *	1997-02-11	1999-11-30	Lilly Co Eli	Medicament for inhibiting glucose metabolism deterioration
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WO1999011269A1 (en) *	1997-09-03	1999-03-11	Eli Lilly And Company	Pyrimidine derivatives
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AU2007312389B2 (en) *	2006-10-19	2012-02-23	F. Hoffmann-La Roche Ag	Aminomethyl-2-imidazoles with affinity with the trace amine associated receptors
RU2009112496A (ru) *	2006-10-19	2010-11-27	Ф. Хоффманн-Ля Рош Аг (Ch)	Аминометил-4-имидазолы
CA2668454A1 (en) *	2006-11-02	2008-05-08	F. Hoffmann-La Roche Ag	Substituted 2-imidazoles
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
CA2672617A1 (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
CN101600700B (zh) *	2007-02-02	2013-08-21	弗·哈夫曼-拉罗切有限公司	作为taar1配体用于cns病症的新的2-氨基噁唑啉
KR101222412B1 (ko) *	2007-02-15	2013-01-15	에프. 호프만-라 로슈 아게	Ｔａａｒ1 리간드로서의 2-아미노옥사졸린
CN101687812A (zh)	2007-07-02	2010-03-31	弗·哈夫曼-拉罗切有限公司	对痕量胺相关受体(taar)具有良好亲和性的2-咪唑啉化合物
CA2691704A1 (en) *	2007-07-03	2009-01-08	F. Hoffmann-La Roche Ag	4-imidazolines and their use as antidepressants
CA2694362A1 (en) *	2007-07-27	2009-02-05	F. Hoffmann-La Roche Ag	2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as taar-ligands
CN101765425A (zh) *	2007-08-02	2010-06-30	弗·哈夫曼-拉罗切有限公司	苯甲酰胺衍生物用于治疗cns障碍的用途
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
CN102083805A (zh) *	2008-07-24	2011-06-01	弗·哈夫曼-拉罗切有限公司	4,5-二氢-唑-2-基衍生物
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
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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 CA CA000339844A patent/CA1138454A/en not_active Expired
- 1979-11-14 AT AT0727079A patent/AT374197B/de not_active IP Right Cessation
- 1979-11-14 SE SE7909392A patent/SE440079B/sv not_active IP Right Cessation
- 1979-11-14 GB GB7939460A patent/GB2039275B/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 IT IT27284/79A patent/IT1127225B/it active
- 1979-11-15 AU AU52873/79A patent/AU541305B1/en not_active Expired
- 1979-11-15 CH CH1021679A patent/CH642965A5/de not_active IP Right Cessation
- 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
NL190553C (nl)	1994-04-18
FR2441625B1 (it)	1981-12-31
DK150142B (da)	1986-12-15
GB2039275A (en)	1980-08-06
NL940011I2 (nl)	1998-05-06
FR2441625A1 (fr)	1980-06-13
ES486349A1 (es)	1980-06-16
CH642965A5 (de)	1984-05-15
AU541305B1 (en)	1985-01-03
NL7908192A (nl)	1980-05-19
DK150142C (da)	1987-06-01
US4323570A (en)	1982-04-06
DK481879A (da)	1980-05-16
IT7927284A0 (it)	1979-11-14
NL190553B (nl)	1993-11-16
SE7909392L (sv)	1980-05-16
NL940011I1 (nl)	1994-08-01
CA1138454A (en)	1982-12-28
IT1127225B (it)	1986-05-21
GB2039275B (en)	1982-11-17
ATA727079A (de)	1983-08-15
AT374197B (de)	1984-03-26

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Publication	Publication Date	Title
SE440079B (sv)	1985-07-15	Substituerade 5-(2-imidazolin-2-yl)-aminopyrimidiner och farmaceutisk komposition
CA2014457C (en)	1999-09-28	Pyrimidine derivatives
US4746664A (en)	1988-05-24	Substituted-3,4-dihydro-4-(2,4,6-trimethoxyphenylimino)-2(1H)-pyrimidones useful as cardiotonic, antihypertensive, cerebrovascular vasodilator and anti-platelet agent
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EP0168262A2 (en)	1986-01-15	Pyrimidine derivatives, processes for preparation thereof and use thereof
US2691655A (en)	1954-10-12	2-amino-4-substituted amino-6-aryl pyrimidines and process of preparing same
JPS6354714B2 (it)	1988-10-28
EP0580753B1 (en)	1995-03-01	Pyrimidine derivatives for enhancing antitumor activity
CN100562518C (zh)	2009-11-25	芳乙烯磺胺类化合物
US4666915A (en)	1987-05-19	2-anilino-1,6-dihydro-6-oxo-5-pyrimidine-carboxylic acid derivatives, process for the preparation thereof, and antiallergic agent containing the same
US3432493A (en)	1969-03-11	Substituted sulfanilamides
JP3252502B2 (ja)	2002-02-04	Ｎ−５保護した２，５−ジアミノ−４，６−ジクロロピリミジンおよびその製造方法
US2465568A (en)	1949-03-29	Pyrimidine compounds
DE2937023A1 (de)	1981-04-02	Neue substituierte 5-(2-imidazolin-2-yl)-aminopyrimidine und verfahren zu deren herstellung
SE449101B (sv)	1987-04-06	1-bensyl-4-/4-(2-pyrimidinylamino)bensyl/-2,3-dioxopiperazinderivat, forfarande for framstellning derav och karcinostatiska medel der de ingar
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JP2597731B2 (ja)	1997-04-09	Ｎ―（２―ヒドロキシエチル）―３―（４―ニトロフェニル）プロピルアミン及びその製造方法