DE1940572A1 - Neue 2-Aminoalkylamino-thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung - Google Patents
Neue 2-Aminoalkylamino-thieno[3,2-d]pyrimidine und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1940572A1 DE1940572A1 DE19691940572 DE1940572A DE1940572A1 DE 1940572 A1 DE1940572 A1 DE 1940572A1 DE 19691940572 DE19691940572 DE 19691940572 DE 1940572 A DE1940572 A DE 1940572A DE 1940572 A1 DE1940572 A1 DE 1940572A1
- Authority
- DE
- Germany
- Prior art keywords
- thieno
- pyrimidine
- morpholino
- radicals
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 29
- -1 ion salts Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000012433 hydrogen halide Substances 0.000 claims description 6
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 6
- ISFDRJXUWTUUMS-UHFFFAOYSA-N n'-(4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)ethane-1,2-diamine Chemical compound C=12SC=CC2=NC(NCCN)=NC=1N1CCOCC1 ISFDRJXUWTUUMS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 4
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- MIOWJQMYIWBJNJ-UHFFFAOYSA-N 1-N-(4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)propane-1,2-diamine Chemical compound NC(CNC=1N=C(C2=C(N1)C=CS2)N2CCOCC2)C MIOWJQMYIWBJNJ-UHFFFAOYSA-N 0.000 claims description 2
- GTVFRCQSZVNTQG-UHFFFAOYSA-N N'-(4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)butane-1,4-diamine Chemical compound NCCCCNC=1N=C(C2=C(N1)C=CS2)N2CCOCC2 GTVFRCQSZVNTQG-UHFFFAOYSA-N 0.000 claims description 2
- FIZAYEURQRAHQB-UHFFFAOYSA-N N'-(4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)propane-1,3-diamine Chemical compound NCCCNC=1N=C(C2=C(N1)C=CS2)N2CCOCC2 FIZAYEURQRAHQB-UHFFFAOYSA-N 0.000 claims description 2
- DTVDLYUYVBMAFZ-UHFFFAOYSA-N N'-methyl-N'-(4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)ethane-1,2-diamine Chemical compound NCCN(C=1N=C(C2=C(N1)C=CS2)N2CCOCC2)C DTVDLYUYVBMAFZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 210000001616 monocyte Anatomy 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000004220 aggregation Methods 0.000 abstract description 4
- 230000002776 aggregation Effects 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 150000001408 amides Chemical class 0.000 abstract description 3
- 150000003949 imides Chemical class 0.000 abstract description 2
- 230000001624 sedative effect Effects 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 230000005792 cardiovascular activity Effects 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 235000019441 ethanol Nutrition 0.000 description 31
- 239000000243 solution Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HKQMXHKNXRNUCF-UHFFFAOYSA-N 4-(2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine Chemical compound C=12SC=CC2=NC(Cl)=NC=1N1CCOCC1 HKQMXHKNXRNUCF-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- AQECFYPZMBRCIA-UHFFFAOYSA-N 2,4-dichlorothieno[3,2-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2SC=CC2=N1 AQECFYPZMBRCIA-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 7
- 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 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical compound NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- DRGCXLJWMQGVJA-UHFFFAOYSA-N pyrimidine;dihydrochloride Chemical compound Cl.Cl.C1=CN=CN=C1 DRGCXLJWMQGVJA-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CJJYUFFJAQRJEE-UHFFFAOYSA-N 2-chloro-4-(4-methylpiperazin-1-yl)thieno[3,2-d]pyrimidine Chemical compound C1CN(C)CCN1C1=NC(Cl)=NC2=C1SC=C2 CJJYUFFJAQRJEE-UHFFFAOYSA-N 0.000 description 2
- VOQGDAKQSIGQJH-UHFFFAOYSA-N 2-chloro-N,N-diethylthieno[3,2-d]pyrimidin-4-amine Chemical compound ClC=1N=C(C2=C(N=1)C=CS2)N(CC)CC VOQGDAKQSIGQJH-UHFFFAOYSA-N 0.000 description 2
- RNKPGHAHWMALFH-UHFFFAOYSA-N 4-(2-chloro-6-methylthieno[3,2-d]pyrimidin-4-yl)morpholine Chemical compound C=12SC(C)=CC2=NC(Cl)=NC=1N1CCOCC1 RNKPGHAHWMALFH-UHFFFAOYSA-N 0.000 description 2
- WISSUVPJBFMAKF-UHFFFAOYSA-N 4-(2-chlorothieno[3,2-d]pyrimidin-4-yl)-2-methylmorpholine Chemical compound C1COC(C)CN1C1=NC(Cl)=NC2=C1SC=C2 WISSUVPJBFMAKF-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
- RJMSJNLLHPZPHW-UHFFFAOYSA-N 5-[(4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)amino]pentan-1-ol Chemical compound OCCCCCNC=1N=C(C2=C(N1)C=CS2)N2CCOCC2 RJMSJNLLHPZPHW-UHFFFAOYSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- CXOYDSMVHHCRAQ-UHFFFAOYSA-N 2-N-(3-aminopropyl)thieno[3,2-d]pyrimidine-2,4-diamine Chemical compound NCCCNC=1N=C(C2=C(N=1)C=CS2)N CXOYDSMVHHCRAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- BWKIIEYLLCXDSV-UHFFFAOYSA-N 2-chloro-4-pyrrolidin-1-ylthieno[3,2-d]pyrimidine Chemical compound ClC=1N=C(C2=C(N1)C=CS2)N2CCCC2 BWKIIEYLLCXDSV-UHFFFAOYSA-N 0.000 description 1
- XGASPHHTVSWLNM-UHFFFAOYSA-N 2-chlorothieno[3,2-d]pyrimidin-4-amine Chemical compound NC1=NC(Cl)=NC2=C1SC=C2 XGASPHHTVSWLNM-UHFFFAOYSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 description 1
- YYIWCGLAEFPUFI-UHFFFAOYSA-N 2-pyrimidin-2-ylethanol Chemical compound OCCC1=NC=CC=N1 YYIWCGLAEFPUFI-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- IUJAXFLKTQXMHJ-UHFFFAOYSA-N 5-(methylamino)pentan-1-ol Chemical compound CNCCCCCO IUJAXFLKTQXMHJ-UHFFFAOYSA-N 0.000 description 1
- XGUUDHYZJGUJMO-UHFFFAOYSA-N 5-[methyl-(4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)amino]pentan-1-ol Chemical compound OCCCCCN(C=1N=C(C2=C(N1)C=CS2)N2CCOCC2)C XGUUDHYZJGUJMO-UHFFFAOYSA-N 0.000 description 1
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
- GADFTULBCMVGOI-UHFFFAOYSA-N CCCCCNC1=NC(NCCN)=NC2=C1SC=C2 Chemical compound CCCCCNC1=NC(NCCN)=NC2=C1SC=C2 GADFTULBCMVGOI-UHFFFAOYSA-N 0.000 description 1
- HNUICOMANAJZGC-UHFFFAOYSA-N CN(CCO)C(N=C1N2CCOCC2)=NC2=C1SC=C2 Chemical compound CN(CCO)C(N=C1N2CCOCC2)=NC2=C1SC=C2 HNUICOMANAJZGC-UHFFFAOYSA-N 0.000 description 1
- 101100048436 Caenorhabditis elegans unc-1 gene Proteins 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- BNGUTDUXKRJETR-UHFFFAOYSA-N Cl.Cl.NCCCCCN(C=1N=C(C2=C(N1)C=CS2)N2CCOCC2)C Chemical compound Cl.Cl.NCCCCCN(C=1N=C(C2=C(N1)C=CS2)N2CCOCC2)C BNGUTDUXKRJETR-UHFFFAOYSA-N 0.000 description 1
- KCOJGLSMKRHDHB-UHFFFAOYSA-N Cl.Cl.NCCNC=1N=C(C2=C(N1)C=CS2)N2CCCC2 Chemical compound Cl.Cl.NCCNC=1N=C(C2=C(N1)C=CS2)N2CCCC2 KCOJGLSMKRHDHB-UHFFFAOYSA-N 0.000 description 1
- XKGIYPPFVKSCKP-UHFFFAOYSA-N N'-(6-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)ethane-1,2-diamine Chemical compound NCCNC=1N=C(C2=C(N=1)C=C(S2)C)N1CCOCC1 XKGIYPPFVKSCKP-UHFFFAOYSA-N 0.000 description 1
- SPWWNNRCLMOPFU-UHFFFAOYSA-N NCCCCCCNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 Chemical compound NCCCCCCNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 SPWWNNRCLMOPFU-UHFFFAOYSA-N 0.000 description 1
- RZCUITQFPRGARY-UHFFFAOYSA-N NCCNC=1N=C(C2=C(N=1)C=CS2)N(CC)CC Chemical compound NCCNC=1N=C(C2=C(N=1)C=CS2)N(CC)CC RZCUITQFPRGARY-UHFFFAOYSA-N 0.000 description 1
- RFEQGSKYECVFOS-UHFFFAOYSA-N NCCNC=1N=C(C2=C(N=1)C=CS2)N1CCC(CC1)O Chemical compound NCCNC=1N=C(C2=C(N=1)C=CS2)N1CCC(CC1)O RFEQGSKYECVFOS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BKWYBTKMDAWEQX-UHFFFAOYSA-N OC(CNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1)C Chemical compound OC(CNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1)C BKWYBTKMDAWEQX-UHFFFAOYSA-N 0.000 description 1
- YSQJYLKFVYDBTJ-UHFFFAOYSA-N OCCCCNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 Chemical compound OCCCCNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 YSQJYLKFVYDBTJ-UHFFFAOYSA-N 0.000 description 1
- IZFSOTXFIHQZJN-UHFFFAOYSA-N OCCCNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 Chemical compound OCCCNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 IZFSOTXFIHQZJN-UHFFFAOYSA-N 0.000 description 1
- NCOZRTIXMXXEGS-UHFFFAOYSA-N OCCNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 Chemical compound OCCNC=1N=C(C2=C(N=1)C=CS2)N1CCOCC1 NCOZRTIXMXXEGS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- MLCJWRIUYXIWNU-UHFFFAOYSA-N ethene-1,2-diamine Chemical compound NC=CN MLCJWRIUYXIWNU-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000008101 lactose Substances 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
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (35)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE754606D BE754606A (fr) | 1969-08-08 | Nouvelles 2-aminoalcoylamino-thieno(3,2-d)pyrimidines et leurs procedesde fabrication | |
| DE19691940572 DE1940572A1 (de) | 1969-08-08 | 1969-08-08 | Neue 2-Aminoalkylamino-thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
| BG17335A BG17969A3 (enrdf_load_stackoverflow) | 1969-08-08 | 1970-07-21 | |
| BG015244A BG17591A3 (bg) | 1969-08-08 | 1970-07-21 | Метод за получаване на нови 2- аминоалкил амино- тиено /3,2-д пиримидини |
| RO69224A RO60647A (enrdf_load_stackoverflow) | 1969-08-08 | 1970-07-28 | |
| RO69223A RO60600A (enrdf_load_stackoverflow) | 1969-08-08 | 1970-07-28 | |
| SU701469618D SU419032A3 (ru) | 1969-08-08 | 1970-07-30 | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 2-А!\\ИНО- АЛ КИЛАМИ НОТИЕНО-[3,2сг]-ПИРИЛ1ИДИ НА |
| SU1669420A SU428607A3 (enrdf_load_stackoverflow) | 1969-08-08 | 1970-07-30 | |
| PH11712*UA PH9574A (en) | 1969-08-08 | 1970-08-04 | 2-(aminoalkyl-amino)-4-amino thieno(3,2-d)-pyrimidines |
| US00060933A US3838121A (en) | 1969-08-08 | 1970-08-04 | 2-(aminoalkyl-amino)-4-amino thieno(3,2-d)pyrimidines |
| NL7011592A NL7011592A (enrdf_load_stackoverflow) | 1969-08-08 | 1970-08-05 | |
| CH1185070A CH547299A (de) | 1969-08-08 | 1970-08-06 | Verfahren zur herstellung neuer 2-aminoalkylamino-thieno(3,2-d)pyrimidine. |
| CH341173A CH547304A (de) | 1969-08-08 | 1970-08-06 | Verfahren zur herstellung neuer 2-aminoalkylamino-thieno(3,2-d)pyrimidine. |
| CH340873A CH547300A (de) | 1969-08-08 | 1970-08-06 | Verfahren zur herstellung neuer 2-aminoalkylamino-thieno(3,2-d)pyrimidine. |
| CH340973A CH547301A (de) | 1969-08-08 | 1970-08-06 | Verfahren zur herstellung neuer 2-aminoalkylamino-thieno(3,2-d)pyrimidine. |
| FI702170A FI51939C (fi) | 1969-08-08 | 1970-08-06 | Menetelmä uusien verihiutaleiden kasautumista estävien 2-aminoalkyylia mino-tieno(3,2-d)pyrimidiinien valmistamiseksi |
| CH341073A CH546251A (de) | 1969-08-08 | 1970-08-06 | Verfahren zur herstellung neuer 2-aminoalkylamino-thieno(3,2-d) pyrimidine. |
| SE7010832A SE386449B (sv) | 1969-08-08 | 1970-08-06 | Forfarande for framstellning av nya 2-aminoalkylamino-tieno(3,2-d)-pyrimidiner |
| ES382552A ES382552A1 (es) | 1969-08-08 | 1970-08-07 | Procedimiento para la preparacion de nuevas 2-aminoalcohi- lamino tieno (3,2-d) pirimidinas. |
| NO3045/70A NO130538C (enrdf_load_stackoverflow) | 1969-08-08 | 1970-08-07 | |
| GB3815070A GB1311499A (en) | 1969-08-08 | 1970-08-07 | Aminoalkylaminothienopyrimidines |
| IL35078A IL35078A (en) | 1969-08-08 | 1970-08-07 | 2-aminoalkylamino-thieno (3,2-d) pyrimidines and their salts,their preparation and pharmaceutical compositions containing them |
| FR7029316A FR2068478B1 (enrdf_load_stackoverflow) | 1969-08-08 | 1970-08-07 | |
| ES382549A ES382549A1 (es) | 1969-08-08 | 1970-08-07 | Un procedimiento para la preparacion de nuevas 2-amino-al- cohil-amino-tieno (3,2-d)piridinas. |
| PL1970142706A PL83617B1 (enrdf_load_stackoverflow) | 1969-08-08 | 1970-08-07 | |
| PL1970175151A PL84258B1 (enrdf_load_stackoverflow) | 1969-08-08 | 1970-08-07 | |
| IE1025/70A IE34687B1 (en) | 1969-08-08 | 1970-08-07 | Aminoalkylaminothieno-pyrimidines |
| ES382551A ES382551A1 (es) | 1969-08-08 | 1970-08-07 | Un procedimiento para la preparacion de nuevas 2-amino-al- cohil-amino-tieno (3,2-d)pirimidinas. |
| AT725170A AT304531B (de) | 1969-08-08 | 1970-08-07 | Verfahren zur Herstellung von neuen 2-Aminoalkylamino-thieno[3,2-d]pyrimidinen und ihren Salzen |
| ZA705482A ZA705482B (en) | 1969-08-08 | 1970-08-07 | Improvements relating to 2-aminoalkyl-amino-thieno(3,2-d)pyrimidines |
| ES382550A ES382550A1 (es) | 1969-08-08 | 1970-08-07 | Procedimiento para la preparacion de nuevas 2-aminoalcohi- lamino-tieno (3,2-d) pirimidinas. |
| ES382548A ES382548A1 (es) | 1969-08-08 | 1970-08-07 | Un procedimiento para la preparacion de nuevas 2-amino-al- cohil-amino-tieno (3,2-d)piridinas. |
| PL1970175153A PL84246B1 (enrdf_load_stackoverflow) | 1969-08-08 | 1970-08-07 | |
| JP45069666A JPS519759B1 (enrdf_load_stackoverflow) | 1969-08-08 | 1970-08-08 | |
| US499460A US3883651A (en) | 1969-08-08 | 1974-08-22 | Pharmaceutical compositions containing a 2-(aminoalkylamino)-4-amino-thieno{8 3,2-d{9 pyrimidine and method of use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691940572 DE1940572A1 (de) | 1969-08-08 | 1969-08-08 | Neue 2-Aminoalkylamino-thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1940572A1 true DE1940572A1 (de) | 1971-02-11 |
Family
ID=5742362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691940572 Pending DE1940572A1 (de) | 1969-08-08 | 1969-08-08 | Neue 2-Aminoalkylamino-thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| BG (1) | BG17969A3 (enrdf_load_stackoverflow) |
| DE (1) | DE1940572A1 (enrdf_load_stackoverflow) |
| PL (3) | PL84258B1 (enrdf_load_stackoverflow) |
| RO (2) | RO60647A (enrdf_load_stackoverflow) |
| SU (2) | SU419032A3 (enrdf_load_stackoverflow) |
| ZA (1) | ZA705482B (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006111549A1 (de) * | 2005-04-21 | 2006-10-26 | Boehringer Ingelheim International Gmbh | Dihydrothienopyrimidine zur behandlung von entzündlichen erkrankungen |
| EP1571146A4 (en) * | 2002-12-10 | 2010-09-01 | Ono Pharmaceutical Co | NITROGENIC HETEROCYCLIC COMPOUNDS AND THEIR MEDICAL USE |
| US8604039B2 (en) | 2006-04-19 | 2013-12-10 | Boehringer Ingelheim International Gmbh | Dihydrothienopyrimidines for the treatment of inflammatory diseases |
| US8637519B2 (en) | 2007-10-19 | 2014-01-28 | Boehringer Ingelheim International Gmbh | Heterocycle-substituted piperazino-dihydrothienopyrimidines |
| US8754073B2 (en) | 2007-10-19 | 2014-06-17 | Boehringer Ingelheim International Gmbh | Substituted piperazino-dihydrothienopyrimidines |
| US9090626B2 (en) | 2007-10-19 | 2015-07-28 | Boehringer Ingelheim International Gmbh | Piperazino-dihydrothienopyrimidine derivatives |
| US9150586B2 (en) | 2011-08-24 | 2015-10-06 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
| US10745411B2 (en) | 2011-08-24 | 2020-08-18 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
-
1969
- 1969-08-08 DE DE19691940572 patent/DE1940572A1/de active Pending
-
1970
- 1970-07-21 BG BG17335A patent/BG17969A3/xx unknown
- 1970-07-28 RO RO69224A patent/RO60647A/ro unknown
- 1970-07-28 RO RO69223A patent/RO60600A/ro unknown
- 1970-07-30 SU SU701469618D patent/SU419032A3/ru active
- 1970-07-30 SU SU1669420A patent/SU428607A3/ru active
- 1970-08-07 PL PL1970175151A patent/PL84258B1/pl unknown
- 1970-08-07 PL PL1970142706A patent/PL83617B1/pl unknown
- 1970-08-07 PL PL1970175153A patent/PL84246B1/pl unknown
- 1970-08-07 ZA ZA705482A patent/ZA705482B/xx unknown
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8153625B2 (en) | 2002-12-10 | 2012-04-10 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic compounds and medicinal use thereof |
| EP1571146A4 (en) * | 2002-12-10 | 2010-09-01 | Ono Pharmaceutical Co | NITROGENIC HETEROCYCLIC COMPOUNDS AND THEIR MEDICAL USE |
| US7723341B2 (en) | 2005-04-21 | 2010-05-25 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of inflammatory diseases |
| US8354531B2 (en) | 2005-04-21 | 2013-01-15 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of inflammatory diseases |
| WO2006111549A1 (de) * | 2005-04-21 | 2006-10-26 | Boehringer Ingelheim International Gmbh | Dihydrothienopyrimidine zur behandlung von entzündlichen erkrankungen |
| TWI380984B (zh) * | 2006-04-19 | 2013-01-01 | Boehringer Ingelheim Int | 用於治療炎性疾病之新穎化合物 |
| EA013108B1 (ru) * | 2006-04-19 | 2010-02-26 | Бёрингер Ингельхайм Интернациональ Гмбх | Дигидротиенопиримидины для лечения воспалительных заболеваний |
| EP2060575A1 (de) * | 2006-04-19 | 2009-05-20 | Boehringer Ingelheim International GmbH | Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen |
| US7511045B2 (en) | 2006-04-19 | 2009-03-31 | Boehringer Ingelheim International Gmbh | Compounds for the treatment of inflammatory diseases |
| JP2008536890A (ja) * | 2006-04-19 | 2008-09-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 炎症性疾患の治療用新規化合物 |
| US8604039B2 (en) | 2006-04-19 | 2013-12-10 | Boehringer Ingelheim International Gmbh | Dihydrothienopyrimidines for the treatment of inflammatory diseases |
| US8637519B2 (en) | 2007-10-19 | 2014-01-28 | Boehringer Ingelheim International Gmbh | Heterocycle-substituted piperazino-dihydrothienopyrimidines |
| US8754073B2 (en) | 2007-10-19 | 2014-06-17 | Boehringer Ingelheim International Gmbh | Substituted piperazino-dihydrothienopyrimidines |
| US9090626B2 (en) | 2007-10-19 | 2015-07-28 | Boehringer Ingelheim International Gmbh | Piperazino-dihydrothienopyrimidine derivatives |
| US9115142B2 (en) | 2007-10-19 | 2015-08-25 | Boehringer Ingelheim International Gmbh | Heterocycle-substituted piperazino-dihydrothienopyrimidines |
| US9150586B2 (en) | 2011-08-24 | 2015-10-06 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
| US10745411B2 (en) | 2011-08-24 | 2020-08-18 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
Also Published As
| Publication number | Publication date |
|---|---|
| SU419032A3 (ru) | 1974-03-05 |
| PL84246B1 (enrdf_load_stackoverflow) | 1976-03-31 |
| ZA705482B (en) | 1971-05-27 |
| RO60647A (enrdf_load_stackoverflow) | 1976-08-15 |
| PL83617B1 (enrdf_load_stackoverflow) | 1975-12-31 |
| PL84258B1 (enrdf_load_stackoverflow) | 1976-03-31 |
| RO60600A (enrdf_load_stackoverflow) | 1976-09-15 |
| BG17969A3 (enrdf_load_stackoverflow) | 1974-03-05 |
| SU428607A3 (enrdf_load_stackoverflow) | 1974-05-15 |
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