JPS6354714B2 - - Google Patents

Info

Publication number: JPS6354714B2
Authority: JP; Japan
Prior art keywords: carbon atoms; group; general formula; halogen; imidazolin
Prior art date: 1978-11-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP54147177A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5592383A (en

Inventor

Sutentsueru Borufugangu

Koonen Eeritsuhi

Furetsuku Borufuganku

Arumaa Ben

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Beiersdorf AG

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

1979-11-15

Publication date

1988-10-28

1979-11-15 Application filed by Beiersdorf AG filed Critical Beiersdorf AG

1980-07-12 Publication of JPS5592383A publication Critical patent/JPS5592383A/ja

1988-10-28 Publication of JPS6354714B2 publication Critical patent/JPS6354714B2/ja

Status Granted legal-status Critical Current

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 38
125000005843 halogen group Chemical group 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 23
-1 alkyl mercaptan Chemical compound 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
125000004414 alkyl thio group Chemical group 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
238000000034 method Methods 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000002585 base Substances 0.000 claims description 7
238000009835 boiling Methods 0.000 claims description 7
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 description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
WPNJAUFVNXKLIM-UHFFFAOYSA-N Moxonidine Chemical compound COC1=NC(C)=NC(Cl)=C1NC1=NCCN1 WPNJAUFVNXKLIM-UHFFFAOYSA-N 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000001447 alkali salts Chemical class 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
241000726103 Atta Species 0.000 claims 2
FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
BUSBKABBRVUHFS-UHFFFAOYSA-N N-(4,5-dihydroimidazol-1-yl)pyrimidin-2-amine Chemical compound N1(C=NCC1)NC1=NC=CC=N1 BUSBKABBRVUHFS-UHFFFAOYSA-N 0.000 claims 1
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
125000002636 imidazolinyl group Chemical group 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000002844 melting Methods 0.000 description 33
230000008018 melting Effects 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
150000005005 aminopyrimidines Chemical group 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
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 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
239000013078 crystal Substances 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
125000001589 carboacyl group Chemical group 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
239000005457 ice water Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
125000000714 pyrimidinyl group Chemical group 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 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 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
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
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
150000001298 alcohols Chemical class 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
230000015572 biosynthetic process Effects 0.000 description 3
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
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
GWPBQZTUTVJCHO-UHFFFAOYSA-N 2-cyclopropyl-5-(4,5-dihydro-1h-imidazol-2-yl)-4,6-dimethoxy-2h-pyrimidin-1-amine Chemical compound NN1C(OC)=C(C=2NCCN=2)C(OC)=NC1C1CC1 GWPBQZTUTVJCHO-UHFFFAOYSA-N 0.000 description 2
UQOKRDJILZMZKU-UHFFFAOYSA-N 2-nitropyrimidine Chemical compound [O-][N+](=O)C1=NC=CC=N1 UQOKRDJILZMZKU-UHFFFAOYSA-N 0.000 description 2
FKRXXAMAHOGYNT-UHFFFAOYSA-N 4,6-dichloro-2-methylpyrimidin-5-amine Chemical compound CC1=NC(Cl)=C(N)C(Cl)=N1 FKRXXAMAHOGYNT-UHFFFAOYSA-N 0.000 description 2
PWAPAZNVFQZPMY-UHFFFAOYSA-N 4-chloro-2-cyclopropyl-5-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2h-pyrimidin-1-amine Chemical compound ClC1=NC(C2CC2)N(N)C(OC)=C1C1=NCCN1 PWAPAZNVFQZPMY-UHFFFAOYSA-N 0.000 description 2
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 2
BFOJCRMEMULDMK-UHFFFAOYSA-N 4-chloro-5-(4,5-dihydro-1h-imidazol-2-yl)-6-ethoxy-2-methyl-2h-pyrimidin-1-amine Chemical compound ClC1=NC(C)N(N)C(OCC)=C1C1=NCCN1 BFOJCRMEMULDMK-UHFFFAOYSA-N 0.000 description 2
GVOLMMVWBFBMMF-UHFFFAOYSA-N 5-(4,5-dihydro-1h-imidazol-2-yl)-4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=NC(N)=NC(OC)=C1C1=NCCN1 GVOLMMVWBFBMMF-UHFFFAOYSA-N 0.000 description 2
150000005008 5-aminopyrimidines Chemical class 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
KRZGKJJPEOUIBI-UHFFFAOYSA-N hydron;thiourea;iodide Chemical compound I.NC(S)=N KRZGKJJPEOUIBI-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000012071 phase Substances 0.000 description 2
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
150000003585 thioureas Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
OPVZXRFEXUBROJ-UHFFFAOYSA-N (4,6-dimethoxypyrimidin-5-yl)thiourea Chemical compound COC1=NC=NC(OC)=C1NC(N)=S OPVZXRFEXUBROJ-UHFFFAOYSA-N 0.000 description 1
FNAOWXNMAKVAIP-UHFFFAOYSA-N 1-[2-(1-amino-4,6-dichloro-2-cyclopropyl-2h-pyrimidin-5-yl)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1C1=C(Cl)N(N)C(C2CC2)N=C1Cl FNAOWXNMAKVAIP-UHFFFAOYSA-N 0.000 description 1
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 1
KEVRHVMWBKFGLO-UHFFFAOYSA-N 2,4-dimethoxypyrimidine Chemical compound COC1=CC=NC(OC)=N1 KEVRHVMWBKFGLO-UHFFFAOYSA-N 0.000 description 1
HOCFRZXMVTXATD-UHFFFAOYSA-N 2-cyclopropyl-5-(4,5-dihydro-1h-imidazol-2-yl)-4,6-bis(methylsulfanyl)-2h-pyrimidin-1-amine Chemical compound NN1C(SC)=C(C=2NCCN=2)C(SC)=NC1C1CC1 HOCFRZXMVTXATD-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
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 description 1
VIVONSUVAHDRLB-UHFFFAOYSA-N 4-chloro-5-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-methyl-2h-pyrimidin-1-amine Chemical compound ClC1=NC(C)N(N)C(OC)=C1C1=NCCN1 VIVONSUVAHDRLB-UHFFFAOYSA-N 0.000 description 1
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 1
GMPGXIMAOQBRHN-UHFFFAOYSA-N 5-(4,5-dihydro-1h-imidazol-2-yl)-4,6-diethoxypyrimidin-2-amine Chemical compound CCOC1=NC(N)=NC(OCC)=C1C1=NCCN1 GMPGXIMAOQBRHN-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
RKAHSAWADCFIMX-UHFFFAOYSA-N NC(N)=S.C1=CN=CN=C1 Chemical class NC(N)=S.C1=CN=CN=C1 RKAHSAWADCFIMX-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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
241000700159 Rattus Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
PMEJIFXRYZEOTM-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-(2,4-dimethoxypyrimidin-5-yl)azanium;iodide Chemical compound [I-].COC1=NC=C([NH+]=C(N)SC)C(OC)=N1 PMEJIFXRYZEOTM-UHFFFAOYSA-N 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
QQYXGRQTVJLPHY-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-(4,6-dimethoxypyrimidin-5-yl)azanium;iodide Chemical compound [I-].COC1=NC=NC(OC)=C1[NH+]=C(N)SC QQYXGRQTVJLPHY-UHFFFAOYSA-N 0.000 description 1
ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
JRYOZJIRAVZGMV-UHFFFAOYSA-N cyclopropanecarboximidamide;hydron;chloride Chemical compound Cl.NC(=N)C1CC1 JRYOZJIRAVZGMV-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
239000003085 diluting agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 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
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000005923 long-lasting effect Effects 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
239000000155 melt Substances 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012022 methylating agents‎ Substances 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 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
239000000047 product Substances 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
230000007017 scission Effects 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005406 washing 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- 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
- 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

JP14717779A 1978-11-15 1979-11-15 Novel substituted 55*22imidazolinee22yl** aminopyrimidine*its manufacture and its use as drug Granted JPS5592383A (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
JPS5592383A JPS5592383A (en)	1980-07-12
JPS6354714B2 true JPS6354714B2 (es)	1988-10-28

Family

ID=6054732

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14717779A Granted JPS5592383A (en)	1978-11-15	1979-11-15	Novel substituted 5522imidazolinee22yl* aminopyrimidine*its manufacture and its use as drug

Country Status (4)

Country	Link
JP (1)	JPS5592383A (es)
BE (1)	BE880042A (es)
DE (1)	DE2849537C2 (es)
ZA (1)	ZA796148B (es)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3016767A1 (de) *	1980-04-30	1981-11-05	Beiersdorf Ag, 2000 Hamburg	Pyrimidylthioharnstoffe, diese enthaltende arzneimittel und deren verwendung
DE3423328A1 (de) *	1984-06-23	1986-01-02	Beiersdorf Ag, 2000 Hamburg	Selbstklebendes pflaster
DE3423293C2 (de) *	1984-06-23	1995-08-24	Lohmann Therapie Syst Lts	Selbstklebendes Pflaster
DE4423177A1 (de) *	1994-07-01	1996-01-04	Kali Chemie Pharma Gmbh	Antihyperglykämisch wirksame Arzneimittel
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
CA2637292A1 (en) *	2006-01-27	2007-08-16	F. Hoffmann-La Roche Ag	Use of 2-imidazoles for the treatment of cns disorders
ATE520685T1 (de) *	2006-06-26	2011-09-15	Chemagis Ltd	Verbessertes verfahren zur herstellung von moxonidin
BRPI0806940A2 (pt)	2007-02-02	2014-05-06	Hoffmann La Roche	2-amino-oxazolinas como ligantes taar1 para distúrbios do snc
CN101616902B (zh)	2007-02-15	2013-03-27	弗·哈夫曼-拉罗切有限公司	作为taar1配体的2-氨基*唑啉类化合物
US8242153B2 (en)	2008-07-24	2012-08-14	Hoffmann-La Roche Inc.	4,5-dihydro-oxazol-2YL derivatives
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
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
RS60825B1 (sr)	2016-03-17	2020-10-30	Hoffmann La Roche	Aktivnost derivata 5-etiol-4-metil-pirazol-3-karboksamida kao agonista taar-a

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE754832A (fr) *	1969-08-14	1971-02-15	Beecham Group Ltd	Iminazolines
BE503170A (es) *	1975-09-02

1978
- 1978-11-15 DE DE2849537A patent/DE2849537C2/de not_active Expired
1979
- 1979-11-14 BE BE0/198116A patent/BE880042A/fr not_active IP Right Cessation
- 1979-11-15 JP JP14717779A patent/JPS5592383A/ja active Granted
- 1979-11-15 ZA ZA00796148A patent/ZA796148B/xx unknown

Also Published As

Publication number	Publication date
DE2849537A1 (de)	1980-05-22
JPS5592383A (en)	1980-07-12
ZA796148B (en)	1980-11-26
BE880042A (fr)	1980-05-14
DE2849537C2 (de)	1983-03-17

Publication	Publication Date	Title
US4323570A (en)	1982-04-06	Substituted aminopyrimidines
JPS6354714B2 (es)	1988-10-28
CA1184188A (en)	1985-03-19	Aryloxypropanolamines
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
JPH0670021B2 (ja)	1994-09-07	医薬品としてのスルホンアミドの使用および新規スルホンアミド
JPH0794447B2 (ja)	1995-10-11	キナゾリン誘導体
KR950000779B1 (ko)	1995-02-02	신경안정적 또는 정신안정적 활성을 가진 피리미디닐-피페라지닐-알킬아졸 유도체
JPH0351706B2 (es)	1991-08-07
CA1218368A (en)	1987-02-24	2-anilino-1,6-dihydro-6-oxo-5-pyrimidinecarboxylic acid derivatives, processes for the preparation thereof, and anti-allergic agent containing the same
EP0009384A1 (en)	1980-04-02	Processes for the preparation of triazinones and condensed triazinones, and compounds so obtained
SK285993B6 (sk)	2008-01-07	Spôsob výroby derivátov pyrimidínu substituovaných aminoskupinou a ich medziprodukty
Curd et al.	1946	71. Synthetic antimalarials. Part IV. 2-Phenylguanidino-4-aminoalkylamino-6-methylpyrimidines
JPH0250110B2 (es)	1990-11-01
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
US6337334B1 (en)	2002-01-08	Pyrimidine derivatives
US3328395A (en)	1967-06-27	6-halo-2-amino substituted-4-sulfanilamido-pyrimidine compounds
US4255574A (en)	1981-03-10	Process for preparing 2,4-diamino-pyrimidines
JPH0546340B2 (es)	1993-07-13
DE2937023A1 (de)	1981-04-02	Neue substituierte 5-(2-imidazolin-2-yl)-aminopyrimidine und verfahren zu deren herstellung
JP2003520762A (ja)	2003-07-08	チオバルビツール酸誘導体の製法
US4434167A (en)	1984-02-28	Pyrimidyl thioureas useful for the treatment of hypertension and hyperlipidemia
JPH05155862A (ja)	1993-06-22	アンジオテンシンｉｉ拮抗薬−含窒素異項環化合物
NO115842B (es)	1968-12-16
CS248717B2 (en)	1987-02-12	Production method of the hydrochloride of the 1-(2-(5 dimethylamino-methyl-2-furylmethylthio)ethyl)p)amino-1-methylamino-2-nitroethylene