CS214813B2 - Method of making the new h2histamine antagonists - Google Patents
Method of making the new h2histamine antagonists Download PDFInfo
- Publication number
- CS214813B2 CS214813B2 CS797734A CS774379A CS214813B2 CS 214813 B2 CS214813 B2 CS 214813B2 CS 797734 A CS797734 A CS 797734A CS 774379 A CS774379 A CS 774379A CS 214813 B2 CS214813 B2 CS 214813B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- amino
- lower alkyl
- pyridyl
- methyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000005557 antagonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- -1 nitro, amino Chemical group 0.000 claims abstract description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 15
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 239000000739 antihistaminic agent Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 13
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 abstract description 10
- 239000001257 hydrogen Substances 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 5
- 150000002431 hydrogen Chemical class 0.000 abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 239000001301 oxygen Chemical group 0.000 abstract description 3
- 229910052760 oxygen Chemical group 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000003282 alkyl amino group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 79
- 239000000203 mixture Substances 0.000 description 50
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 235000019441 ethanol Nutrition 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 23
- 229960001340 histamine Drugs 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000010992 reflux Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 230000004071 biological effect Effects 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000027119 gastric acid secretion Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- RHHFNUQDIRYPSI-UHFFFAOYSA-N n-[6-oxo-5-(pyridin-3-ylmethyl)-1h-pyrimidin-2-yl]nitramide Chemical compound N1C(N[N+](=O)[O-])=NC(=O)C(CC=2C=NC=CC=2)=C1 RHHFNUQDIRYPSI-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000006308 propyl amino group Chemical group 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- KZRZMQRVMQVELJ-UHFFFAOYSA-N 2-methylsulfanyl-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound O=C1NC(SC)=NC=C1CC1=CC=CN=C1 KZRZMQRVMQVELJ-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 4
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229960000582 mepyramine Drugs 0.000 description 4
- 239000011343 solid material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229940125715 antihistaminic agent Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 3
- 229960003151 mercaptamine Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- NENUHAOLAJUKLM-UHFFFAOYSA-N 1-(3-bromophenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC(Br)=C1 NENUHAOLAJUKLM-UHFFFAOYSA-N 0.000 description 2
- XDVTXBGLTDADQR-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methylsulfanyl]ethanamine Chemical compound COC1=CC=CC=C1CSCCN XDVTXBGLTDADQR-UHFFFAOYSA-N 0.000 description 2
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 2
- OAZIAOCXVZMCCR-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)prop-2-enoic acid Chemical compound CC1=CC=C(C=CC(O)=O)C=N1 OAZIAOCXVZMCCR-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- AGNFWIZBEATIAK-UHFFFAOYSA-N 4-phenylbutylamine Chemical compound NCCCCC1=CC=CC=C1 AGNFWIZBEATIAK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 102000003834 Histamine H1 Receptors Human genes 0.000 description 2
- 108090000110 Histamine H1 Receptors Proteins 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 2
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 2
- 229960003291 chlorphenamine Drugs 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 229960000520 diphenhydramine Drugs 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- UPQKGGCHMZDTBL-UHFFFAOYSA-N ethyl 3-(6-methylpyridin-3-yl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(C)N=C1 UPQKGGCHMZDTBL-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- 239000000938 histamine H1 antagonist Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- CXKNKSIXOWIZTJ-UHFFFAOYSA-N 1-(3-bromo-4-methoxyphenyl)-n,n-dimethylmethanamine Chemical compound COC1=CC=C(CN(C)C)C=C1Br CXKNKSIXOWIZTJ-UHFFFAOYSA-N 0.000 description 1
- RFEDQTSVZVRTGH-UHFFFAOYSA-N 1-(4-bromophenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=C(Br)C=C1 RFEDQTSVZVRTGH-UHFFFAOYSA-N 0.000 description 1
- UAWVMPOAIVZWFQ-UHFFFAOYSA-N 1-(chloromethyl)-2-methoxybenzene Chemical compound COC1=CC=CC=C1CCl UAWVMPOAIVZWFQ-UHFFFAOYSA-N 0.000 description 1
- ZPCJPJQUVRIILS-UHFFFAOYSA-N 1-bromo-3-(bromomethyl)benzene Chemical compound BrCC1=CC=CC(Br)=C1 ZPCJPJQUVRIILS-UHFFFAOYSA-N 0.000 description 1
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 1
- 150000008081 1H-pyrimidin-4-ones Chemical class 0.000 description 1
- FHCUIVUFAWWYGB-UHFFFAOYSA-N 2-(4-aminobutyl)aniline Chemical compound NCCCCC1=CC=CC=C1N FHCUIVUFAWWYGB-UHFFFAOYSA-N 0.000 description 1
- AAEWYCZRXWDEJN-UHFFFAOYSA-N 2-(4-phenylbutylamino)-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one;dihydrate Chemical compound O.O.N=1C=C(CC=2C=NC=CC=2)C(=O)NC=1NCCCCC1=CC=CC=C1 AAEWYCZRXWDEJN-UHFFFAOYSA-N 0.000 description 1
- XAWFUEGPSVHAMP-UHFFFAOYSA-N 2-[2-[(2-methoxyphenyl)methylsulfanyl]ethylamino]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1CSCCNC(NC1=O)=NC=C1CC1=CC=CN=C1 XAWFUEGPSVHAMP-UHFFFAOYSA-N 0.000 description 1
- GMRVRZAZPWOQMR-UHFFFAOYSA-N 2-[2-[[3-[(dimethylamino)methyl]phenyl]methylsulfanyl]ethylamino]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound CN(C)CC1=CC=CC(CSCCNC=2NC(=O)C(CC=3C=NC=CC=3)=CN=2)=C1 GMRVRZAZPWOQMR-UHFFFAOYSA-N 0.000 description 1
- RQAAQAULJQIBFD-UHFFFAOYSA-N 2-[[3-[(dimethylamino)methyl]phenyl]methylsulfanyl]ethanamine Chemical compound CN(C)CC1=CC=CC(CSCCN)=C1 RQAAQAULJQIBFD-UHFFFAOYSA-N 0.000 description 1
- CXUQTBGTUZORSO-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]-2-methoxyphenyl]methylsulfanyl]ethanamine Chemical compound COC1=CC=C(CN(C)C)C=C1CSCCN CXUQTBGTUZORSO-UHFFFAOYSA-N 0.000 description 1
- PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 description 1
- LGROUIFCRUBNIJ-UHFFFAOYSA-N 2-bromo-4-(chloromethyl)-1-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1Br LGROUIFCRUBNIJ-UHFFFAOYSA-N 0.000 description 1
- ZEQMMXMSZSMEND-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]phenoxy]propan-1-amine Chemical compound CN(C)CC1=CC=CC(OCCCN)=C1 ZEQMMXMSZSMEND-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
- SAFNULYMNFGMLA-UHFFFAOYSA-N 4-(2-aminophenyl)butanenitrile Chemical compound NC1=CC=CC=C1CCCC#N SAFNULYMNFGMLA-UHFFFAOYSA-N 0.000 description 1
- GDRNNGAOPZOKFM-UHFFFAOYSA-N 4-(4-bromobutyl)isoindole-1,3-dione Chemical compound BrCCCCC1=CC=CC2=C1C(=O)NC2=O GDRNNGAOPZOKFM-UHFFFAOYSA-N 0.000 description 1
- RIVXXVQFLWDWLB-UHFFFAOYSA-N 4-methyl-2H-pyrimidine-1-carbaldehyde Chemical compound CC1=NCN(C=C1)C=O RIVXXVQFLWDWLB-UHFFFAOYSA-N 0.000 description 1
- IBRVMLVSNYQCGL-UHFFFAOYSA-N 5-[(6-methylpyridin-3-yl)methyl]-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound C1=NC(C)=CC=C1CC1=CNC(=S)NC1=O IBRVMLVSNYQCGL-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- QDQKQNXEXMHPNE-UHFFFAOYSA-N C1=CC=C(C=C1)CSCCNC2=NC=C(C(=O)N2)CC3=CN=CC=C3 Chemical compound C1=CC=C(C=C1)CSCCNC2=NC=C(C(=O)N2)CC3=CN=CC=C3 QDQKQNXEXMHPNE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229940124056 Histamine H1 receptor antagonist Drugs 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- 102000000543 Histamine Receptors Human genes 0.000 description 1
- 108010002059 Histamine Receptors Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 125000004633 N-oxo-pyridyl group Chemical group 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 108010079943 Pentagastrin Proteins 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 208000031709 Skin Manifestations Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- 208000001871 Tachycardia Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000004768 bromobenzenes Chemical class 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 description 1
- YJJLOESDBPRZIP-UHFFFAOYSA-N diethyl 2-(2-cyanoethyl)propanedioate Chemical compound CCOC(=O)C(CCC#N)C(=O)OCC YJJLOESDBPRZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
- SFPIPAREYAMJEW-UHFFFAOYSA-N ethyl 2-formyl-3-pyridin-3-ylpropanoate Chemical compound CCOC(=O)C(C=O)CC1=CC=CN=C1 SFPIPAREYAMJEW-UHFFFAOYSA-N 0.000 description 1
- ZABMIGDVOIATQB-UHFFFAOYSA-N ethyl 3-(6-methylpyridin-3-yl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(C)N=C1 ZABMIGDVOIATQB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- KWBSLRQDOHBJPQ-UHFFFAOYSA-N n-[5-[(6-methylpyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(C)=CC=C1CC1=CN=C(N[N+]([O-])=O)NC1=O KWBSLRQDOHBJPQ-UHFFFAOYSA-N 0.000 description 1
- GBZXGMIWFGEOGL-UHFFFAOYSA-N n-benzyl-n',n'-dimethylmethanediamine Chemical compound CN(C)CNCC1=CC=CC=C1 GBZXGMIWFGEOGL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 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
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7844260 | 1978-11-13 | ||
| GB7929013 | 1979-08-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214813B2 true CS214813B2 (en) | 1982-06-25 |
Family
ID=26269556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS797734A CS214813B2 (en) | 1978-11-13 | 1979-11-13 | Method of making the new h2histamine antagonists |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4496567A (ro) |
| EP (1) | EP0013071B1 (ro) |
| JP (1) | JPS55500898A (ro) |
| AU (1) | AU534802B2 (ro) |
| CA (1) | CA1137984A (ro) |
| CS (1) | CS214813B2 (ro) |
| DD (1) | DD146953A5 (ro) |
| DE (1) | DE2966413D1 (ro) |
| DK (1) | DK298180A (ro) |
| ES (1) | ES485912A1 (ro) |
| FI (1) | FI793533A7 (ro) |
| GR (1) | GR78338B (ro) |
| HU (1) | HU182740B (ro) |
| IE (1) | IE49205B1 (ro) |
| IL (1) | IL58676A (ro) |
| NO (1) | NO793642L (ro) |
| NZ (1) | NZ192096A (ro) |
| PH (1) | PH15579A (ro) |
| PL (1) | PL126169B1 (ro) |
| PT (1) | PT70441A (ro) |
| RO (1) | RO78491A (ro) |
| WO (1) | WO1980000966A1 (ro) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1140129A (en) * | 1979-08-21 | 1983-01-25 | Ronald J. King | 4-pyrimidone derivatives |
| EP0071434B1 (en) * | 1981-07-24 | 1987-01-28 | Glaxo Group Limited | Heterocyclic derivatives |
| US4745110A (en) * | 1983-04-29 | 1988-05-17 | Rorer Pharmaceutical Corporation | Bicyclic benzenoid aminoalkylene ethers and thioethers, pharmaceutical compositions and use |
| GB8318638D0 (en) * | 1983-07-09 | 1983-08-10 | Smith Kline French Lab | Chemical compounds |
| GB8320505D0 (en) * | 1983-07-29 | 1983-09-01 | Smith Kline French Lab | Chemical compounds |
| US4772704A (en) * | 1983-09-21 | 1988-09-20 | Bristol-Myers Company | 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity |
| GB8332091D0 (en) * | 1983-12-01 | 1984-01-11 | Smith Kline French Lab | Chemical compounds |
| GB8421427D0 (en) * | 1984-08-23 | 1984-09-26 | Smith Kline French Lab | Chemical compounds |
| JO1410B1 (en) * | 1984-11-03 | 1986-11-30 | سميث كلاين اند فرينش لابوراتوريز ليمتد | Compounds |
| JPS61155373A (ja) * | 1984-12-28 | 1986-07-15 | Yamanouchi Pharmaceut Co Ltd | 新規な２−置換アミノ−４（１ｈ）−ピリミドン誘導体及びその製造法 |
| JP2807577B2 (ja) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | 環状アミド誘導体 |
| EP3909449A1 (en) | 2020-05-11 | 2021-11-17 | Bisaf Spolka Z Ograniczona Odpowiedzialnoscia | Protective filtering half mask |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980781A (en) * | 1966-03-31 | 1976-09-14 | Imperial Chemical Industries Limited | Fungicidal composition and method containing 2-amino-pyrimidines |
| GB1223686A (en) * | 1967-02-24 | 1971-03-03 | Ici Ltd | Salts of pyrimidine derivatives and the use thereof as fungicides |
| GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| IN146736B (ro) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
| US4145546A (en) * | 1975-10-02 | 1979-03-20 | Smith Kline & French Laboratories Limited | 4-Pyrimidone compounds |
| MW5076A1 (en) * | 1975-12-29 | 1978-02-08 | Smith Kline French Lab | Pharmacologicalle active compounds |
| US4154834A (en) * | 1975-12-29 | 1979-05-15 | Smith Kline & French Laboratories Limited | Substituted isocytosines having histamine H2 -antagonist activity |
| US4117131A (en) * | 1976-12-07 | 1978-09-26 | Warner-Lambert Company | Method of inhibiting gastric acid secretions with 2-(4-pyrimidinyl)thioacetamides |
| GB1604674A (en) * | 1977-05-17 | 1981-12-16 | Allen & Hanburys Ltd | Aminoalkyl-benzene derivatives |
| ZA793443B (en) * | 1978-07-26 | 1980-12-31 | Glaxo Group Ltd | Heterocyclic derivatives |
-
1979
- 1979-11-06 US US06/091,850 patent/US4496567A/en not_active Expired - Lifetime
- 1979-11-08 JP JP50182279A patent/JPS55500898A/ja active Pending
- 1979-11-08 DE DE7979302509T patent/DE2966413D1/de not_active Expired
- 1979-11-08 EP EP79302509A patent/EP0013071B1/en not_active Expired
- 1979-11-08 CA CA000339434A patent/CA1137984A/en not_active Expired
- 1979-11-08 WO PCT/GB1979/000184 patent/WO1980000966A1/en not_active Ceased
- 1979-11-09 IL IL58676A patent/IL58676A/xx unknown
- 1979-11-09 PH PH23272A patent/PH15579A/en unknown
- 1979-11-12 PT PT70441A patent/PT70441A/pt unknown
- 1979-11-12 IE IE2169/79A patent/IE49205B1/en unknown
- 1979-11-12 DD DD79216837A patent/DD146953A5/de unknown
- 1979-11-12 FI FI793533A patent/FI793533A7/fi not_active Application Discontinuation
- 1979-11-12 PL PL1979219563A patent/PL126169B1/pl unknown
- 1979-11-12 NO NO793642A patent/NO793642L/no unknown
- 1979-11-12 NZ NZ192096A patent/NZ192096A/xx unknown
- 1979-11-12 GR GR60483A patent/GR78338B/el unknown
- 1979-11-12 HU HU79SI1728A patent/HU182740B/hu unknown
- 1979-11-12 AU AU52722/79A patent/AU534802B2/en not_active Ceased
- 1979-11-13 RO RO7999212A patent/RO78491A/ro unknown
- 1979-11-13 ES ES485912A patent/ES485912A1/es not_active Expired
- 1979-11-13 CS CS797734A patent/CS214813B2/cs unknown
-
1980
- 1980-07-10 DK DK298180A patent/DK298180A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU534802B2 (en) | 1984-02-16 |
| EP0013071B1 (en) | 1983-11-16 |
| NO793642L (no) | 1980-05-14 |
| ES485912A1 (es) | 1980-07-01 |
| WO1980000966A1 (en) | 1980-05-15 |
| RO78491A (ro) | 1982-02-26 |
| DE2966413D1 (en) | 1983-12-22 |
| HU182740B (en) | 1984-03-28 |
| NZ192096A (en) | 1981-11-19 |
| JPS55500898A (ro) | 1980-11-06 |
| CA1137984A (en) | 1982-12-21 |
| PL219563A1 (ro) | 1980-12-01 |
| DD146953A5 (de) | 1981-03-11 |
| PT70441A (en) | 1979-12-01 |
| PH15579A (en) | 1983-02-17 |
| IE49205B1 (en) | 1985-08-21 |
| GR78338B (ro) | 1984-09-26 |
| FI793533A7 (fi) | 1981-01-01 |
| US4496567A (en) | 1985-01-29 |
| IL58676A (en) | 1983-07-31 |
| PL126169B1 (en) | 1983-07-30 |
| AU5272279A (en) | 1980-05-22 |
| IE792169L (en) | 1980-05-13 |
| DK298180A (da) | 1980-07-10 |
| EP0013071A1 (en) | 1980-07-09 |
| IL58676A0 (en) | 1980-02-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS214813B2 (en) | Method of making the new h2histamine antagonists | |
| PL118708B1 (en) | Process for preparing novel pyrimidones | |
| AU596410B2 (en) | Novel dopamine beta hydroxylase inhibitors | |
| US4083983A (en) | Alkoxy pyridine compounds | |
| HU184259B (en) | Process for producing 2-imidazoline derivatives | |
| US4255428A (en) | 5-(Hydroxypyridylalkyl)-4-pyrimidones | |
| HU212302B (en) | Process for producing imidazole guanidine derivatives and pharmaceutical compositions containing them | |
| HU216973B (hu) | Eljárás imidazolszármazékok előállítására | |
| HU180081B (en) | Process for producing hystamine antagonic 2-amino-pirimidone derivatives | |
| HU213212B (en) | Process for producing acid additional salts of 4-amino-2-ureidopyrimidine-5-carboxylic acid amide derivatives and pharmaceutical compositions comprising the same | |
| US4156727A (en) | Alkoxy pyridine compounds | |
| HU176882B (en) | Process for preparing bis-guanidino-substituted alkane derivatives | |
| EP0086647B1 (en) | Pyrimidone compounds, their preparation, and pharmaceutical compositions containing them | |
| US4113868A (en) | 5,6-dihydropyrimidin-4(3h)one derivatives, and antiedema compositions and methods employing them | |
| HU176328B (en) | Process for preparing isothiocarbamide derivatives | |
| US4810800A (en) | Novel imidazole dopamine beta hydroxylase inhibitors | |
| EP0017680B1 (en) | Pyrimidone derivatives, process for preparing them and pharmaceutical compositions containing them | |
| US4036972A (en) | 2-(N-thienylmethyl-phenylamino)-imidazolines-(2) and salts thereof | |
| US4234590A (en) | Thiosubstituted pyridines | |
| US4110456A (en) | 4-substituted-2-arylimidazoles | |
| JP2750578B2 (ja) | 新規な（アリール又はヘテロ芳香族メチル）‐２，２’‐ビ‐１ｈ‐イミダゾール類 | |
| KR830000313B1 (ko) | 피리미돈의 제조방법 | |
| CS208497B2 (cs) | Způsob výroby pyrimidonů | |
| KR820001993B1 (ko) | 히스타민h₂수용체 길항작용을 가진 니트로 화합물의 제조방법 | |
| HU197895B (en) | Process for producing 1,4-dihydropyridine derivatives and pharmaceutical compositions comprising same as active ingredient |