NO301476B1 - N-£3-£2-(1H-imidazol-1-yl)etoksy|-4-(2-tienyl)-2-pyrimidinamin og farmakologisk akseptable salter derav - Google Patents
N-£3-£2-(1H-imidazol-1-yl)etoksy|-4-(2-tienyl)-2-pyrimidinamin og farmakologisk akseptable salter derav Download PDFInfo
- Publication number
- NO301476B1 NO301476B1 NO924760A NO924760A NO301476B1 NO 301476 B1 NO301476 B1 NO 301476B1 NO 924760 A NO924760 A NO 924760A NO 924760 A NO924760 A NO 924760A NO 301476 B1 NO301476 B1 NO 301476B1
- Authority
- NO
- Norway
- Prior art keywords
- ethoxy
- pyrimidinamine
- imidazol
- thienyl
- phenyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 13
- LMUUYPFNADZBFI-UHFFFAOYSA-N n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine Chemical compound C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 LMUUYPFNADZBFI-UHFFFAOYSA-N 0.000 claims abstract description 27
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- -1 malinate Chemical compound 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- 229960005070 ascorbic acid Drugs 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- UREGXELIFHQSMF-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine Chemical compound OC(=O)C(O)C(O)C(O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 UREGXELIFHQSMF-UHFFFAOYSA-N 0.000 claims description 2
- DYZDEXDYSPILOP-UHFFFAOYSA-N 2-hydroxybutanedioic acid;n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine Chemical compound OC(=O)C(O)CC(O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 DYZDEXDYSPILOP-UHFFFAOYSA-N 0.000 claims description 2
- UNWIGRMXPIGPHI-UHFFFAOYSA-N 2-hydroxypropanoic acid;n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine Chemical compound CC(O)C(O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 UNWIGRMXPIGPHI-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 239000002211 L-ascorbic acid Substances 0.000 claims description 2
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 2
- ZKBJNTKUKOLJHG-UHFFFAOYSA-N acetic acid;n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine Chemical compound CC(O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 ZKBJNTKUKOLJHG-UHFFFAOYSA-N 0.000 claims description 2
- YEHQRAWQDAXCAS-UHFFFAOYSA-N but-2-enedioic acid;n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine Chemical compound OC(=O)C=CC(O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 YEHQRAWQDAXCAS-UHFFFAOYSA-N 0.000 claims description 2
- KLZYFOOZTCASLG-UHFFFAOYSA-N n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine;hydrobromide Chemical compound Br.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 KLZYFOOZTCASLG-UHFFFAOYSA-N 0.000 claims description 2
- RVAWITQBTWOVQW-UHFFFAOYSA-N n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 RVAWITQBTWOVQW-UHFFFAOYSA-N 0.000 claims description 2
- KGGPJQXYNSXCQC-UHFFFAOYSA-N n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine;phosphoric acid Chemical compound OP(O)(O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 KGGPJQXYNSXCQC-UHFFFAOYSA-N 0.000 claims description 2
- UCHJQELKMVNLJM-UHFFFAOYSA-N n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine;sulfamic acid Chemical compound NS(O)(=O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 UCHJQELKMVNLJM-UHFFFAOYSA-N 0.000 claims description 2
- XKGOKJPUKUVPOL-UHFFFAOYSA-N n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine;sulfuric acid Chemical compound OS(O)(=O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 XKGOKJPUKUVPOL-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 229940022663 acetate Drugs 0.000 claims 1
- 229940072107 ascorbate Drugs 0.000 claims 1
- 229940050411 fumarate Drugs 0.000 claims 1
- 229940050410 gluconate Drugs 0.000 claims 1
- JTWFWMSVZFGQAH-UHFFFAOYSA-N n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 JTWFWMSVZFGQAH-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229940086735 succinate Drugs 0.000 claims 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 abstract description 2
- 239000000924 antiasthmatic agent Substances 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 89
- 150000001875 compounds Chemical class 0.000 description 81
- 235000019441 ethanol Nutrition 0.000 description 44
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 30
- 239000013078 crystal Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- 241000282472 Canis lupus familiaris Species 0.000 description 18
- 229960001340 histamine Drugs 0.000 description 17
- 208000006673 asthma Diseases 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 210000002381 plasma Anatomy 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- 239000013566 allergen Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000036470 plasma concentration Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 206010020751 Hypersensitivity Diseases 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 206010052428 Wound Diseases 0.000 description 6
- 208000027418 Wounds and injury Diseases 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- LMXDEBKXFDXSGZ-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethoxy]phenyl]-4-pyridin-4-ylpyrimidin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=CC(C=2C=CN=CC=2)=N1 LMXDEBKXFDXSGZ-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 230000007815 allergy Effects 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 210000003630 histaminocyte Anatomy 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- NUBOEAKSRADQKP-UHFFFAOYSA-N 2-methyl-4-n-(4-pyridin-4-ylpyrimidin-2-yl)benzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.C1=C(N)C(C)=CC(NC=2N=C(C=CN=2)C=2C=CN=CC=2)=C1 NUBOEAKSRADQKP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 102000008100 Human Serum Albumin Human genes 0.000 description 3
- 108091006905 Human Serum Albumin Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000001045 blue dye Substances 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- PPCXPLRJNAOICA-UHFFFAOYSA-N 2-[3-(2-imidazol-1-ylethoxy)phenyl]guanidine;dihydrochloride Chemical compound Cl.Cl.NC(=N)NC1=CC=CC(OCCN2C=NC=C2)=C1 PPCXPLRJNAOICA-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- NXYSVZGMDFMOJJ-UHFFFAOYSA-N 3-(dimethylamino)-1-thiophen-2-ylprop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=CS1 NXYSVZGMDFMOJJ-UHFFFAOYSA-N 0.000 description 2
- LIFAQMGORKPVDH-UHFFFAOYSA-N 7-ethoxycoumarin Chemical compound C1=CC(=O)OC2=CC(OCC)=CC=C21 LIFAQMGORKPVDH-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 201000009961 allergic asthma Diseases 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000001088 anti-asthma Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 210000003651 basophil Anatomy 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 229960005069 calcium Drugs 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000004856 capillary permeability Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000019693 cherries Nutrition 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 108010089616 dinitrophenol-ovalbumin Proteins 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000000174 gluconic acid Substances 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229940091250 magnesium supplement Drugs 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 229940078693 1-myristylpicolinium Drugs 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- ZCTSINFCZHUVLI-UHFFFAOYSA-M 4-methyl-1-tetradecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+]1=CC=C(C)C=C1 ZCTSINFCZHUVLI-UHFFFAOYSA-M 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000238713 Dermatophagoides farinae Species 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 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 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- GOQQDHFFYAJLBA-UHFFFAOYSA-N butanedioic acid;n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine Chemical compound OC(=O)CCC(O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 GOQQDHFFYAJLBA-UHFFFAOYSA-N 0.000 description 1
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007958 cherry flavor Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000007950 delayed release tablet Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- YQZBAXDVDZTKEQ-UHFFFAOYSA-N loxapine succinate Chemical group [H+].[H+].[O-]C(=O)CCC([O-])=O.C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 YQZBAXDVDZTKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 229940062713 mite extract Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- BUHQNLLMKPUGBV-IFWQJVLJSA-N n-[3-(2-imidazol-1-ylethoxy)phenyl]-4-thiophen-2-ylpyrimidin-2-amine;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C=1C=CC(NC=2N=C(C=CN=2)C=2SC=CC=2)=CC=1OCCN1C=CN=C1 BUHQNLLMKPUGBV-IFWQJVLJSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- WZODLFCLKIXWGA-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)C)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] WZODLFCLKIXWGA-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/816,335 US5162328A (en) | 1991-12-31 | 1991-12-31 | N-[3-[2-(1H-imidazol-1-yl)ethoxy]phenyl]-4-(2-thienyl)-2-pyrimidinamine and pharmacologically acceptable salts |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO924760D0 NO924760D0 (no) | 1992-12-09 |
| NO924760L NO924760L (no) | 1993-07-01 |
| NO301476B1 true NO301476B1 (no) | 1997-11-03 |
Family
ID=25220310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO924760A NO301476B1 (no) | 1991-12-31 | 1992-12-09 | N-£3-£2-(1H-imidazol-1-yl)etoksy|-4-(2-tienyl)-2-pyrimidinamin og farmakologisk akseptable salter derav |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5162328A (fr) |
| EP (1) | EP0549880B1 (fr) |
| JP (1) | JPH05271227A (fr) |
| KR (1) | KR930012761A (fr) |
| AT (1) | ATE171178T1 (fr) |
| AU (1) | AU651539B2 (fr) |
| CA (1) | CA2086357A1 (fr) |
| DE (1) | DE69227015T2 (fr) |
| DK (1) | DK0549880T3 (fr) |
| ES (1) | ES2121809T3 (fr) |
| FI (1) | FI925951A (fr) |
| HU (1) | HUT66943A (fr) |
| NO (1) | NO301476B1 (fr) |
| NZ (1) | NZ245513A (fr) |
| SG (1) | SG47556A1 (fr) |
| ZA (1) | ZA9210120B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007053776A1 (fr) * | 2005-11-03 | 2007-05-10 | Sgx Pharmaceuticals, Inc. | Modulateurs de kinase de type pyrimidinylthiophène |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3751742T3 (de) * | 1986-01-13 | 2002-11-21 | American Cyanamid Co., Wayne | 4,5,6-Substituierte 2-Pyrimidinamine |
| US4788195A (en) * | 1986-01-13 | 1988-11-29 | American Cyanamid Company | 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines |
-
1991
- 1991-12-31 US US07/816,335 patent/US5162328A/en not_active Expired - Fee Related
-
1992
- 1992-11-23 EP EP92119890A patent/EP0549880B1/fr not_active Expired - Lifetime
- 1992-11-23 DE DE69227015T patent/DE69227015T2/de not_active Expired - Fee Related
- 1992-11-23 ES ES92119890T patent/ES2121809T3/es not_active Expired - Lifetime
- 1992-11-23 DK DK92119890T patent/DK0549880T3/da active
- 1992-11-23 AT AT92119890T patent/ATE171178T1/de not_active IP Right Cessation
- 1992-11-23 SG SG1996002818A patent/SG47556A1/en unknown
- 1992-12-09 NO NO924760A patent/NO301476B1/no unknown
- 1992-12-18 NZ NZ24551392A patent/NZ245513A/en unknown
- 1992-12-24 JP JP4357370A patent/JPH05271227A/ja active Pending
- 1992-12-29 CA CA002086357A patent/CA2086357A1/fr not_active Abandoned
- 1992-12-30 FI FI925951A patent/FI925951A/fi unknown
- 1992-12-30 KR KR1019920027617A patent/KR930012761A/ko not_active Application Discontinuation
- 1992-12-30 ZA ZA9210120A patent/ZA9210120B/xx unknown
- 1992-12-30 AU AU30462/92A patent/AU651539B2/en not_active Ceased
- 1992-12-30 HU HU9204172A patent/HUT66943A/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2086357A1 (fr) | 1993-07-01 |
| FI925951A (fi) | 1993-07-01 |
| NO924760L (no) | 1993-07-01 |
| ZA9210120B (en) | 1994-04-12 |
| US5162328A (en) | 1992-11-10 |
| EP0549880A1 (fr) | 1993-07-07 |
| AU651539B2 (en) | 1994-07-21 |
| EP0549880B1 (fr) | 1998-09-16 |
| DE69227015D1 (de) | 1998-10-22 |
| DK0549880T3 (da) | 1999-06-14 |
| SG47556A1 (en) | 1998-04-17 |
| HUT66943A (en) | 1995-01-30 |
| HU9204172D0 (en) | 1993-04-28 |
| AU3046292A (en) | 1993-07-08 |
| ES2121809T3 (es) | 1998-12-16 |
| FI925951A0 (fi) | 1992-12-30 |
| DE69227015T2 (de) | 1999-03-25 |
| ATE171178T1 (de) | 1998-10-15 |
| NO924760D0 (no) | 1992-12-09 |
| KR930012761A (ko) | 1993-07-21 |
| JPH05271227A (ja) | 1993-10-19 |
| NZ245513A (en) | 1994-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0233461B2 (fr) | 2-Pyrimidinamines substituées en 4,5 et 6 | |
| FI105914B (fi) | Menetelmä valmistaa farmaseuttisesti vaikuttavaa 1-[(4-kloorifenyyli)fenyylimetyyli]-4-[(4-metyylifenyyli)sulfonyyli]piperatsiinin vasemmalle tai oikealle kiertävää enantiomeeria | |
| DE60118564T2 (de) | Propan-1,3-dion-derivate | |
| EP1440976A1 (fr) | Aminoacides modifiés, médicaments contenant ces composés et leur procédé de production | |
| CN1997640A (zh) | 作为代谢调节剂的经取代芳基和杂芳基衍生物及其相关病症的预防和治疗 | |
| JP2010502751A (ja) | キナーゼ阻害物質、およびキナーゼ阻害物質の使用および同定方法 | |
| CN102918036A (zh) | 用作β-分泌酶(BACE)抑制剂的5-氨基-3,6-二氢-1H-吡嗪-2-酮衍生物 | |
| NO158419B (no) | Analogifremgangsmaate til fremstilling av terapeutisk aktive 1,2-diaminocyklobuten-3,4-dioner. | |
| EP2985283B1 (fr) | Composé anti-angiogenèse, intermédiaire et son utilisation | |
| EP1163239A1 (fr) | Amides d'aminoacides modifies comme antagonistes de la cgrp | |
| WO2007000320A2 (fr) | Procede pour le diagnostic de maladies rhumatismales | |
| JP6864327B2 (ja) | 脂質過酸化誘発性疾患の治療薬およびそのスクリーニング方法 | |
| WO2023087611A1 (fr) | Sel d'ébastine, procédé de préparation associé et son application | |
| NO173826B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive 4-fenylpiperidinforbindelser | |
| CN116194096A (zh) | 一种用于预防和治疗听力损伤的分拣蛋白拮抗剂 | |
| AU2015318324A1 (en) | Crystalline forms of tyrosine kinase inhibitors and their salts | |
| NO149311B (no) | Analogifremgangsmaate til fremstilling av terapeutisk aktive propanolindolderivater | |
| NO301476B1 (no) | N-£3-£2-(1H-imidazol-1-yl)etoksy|-4-(2-tienyl)-2-pyrimidinamin og farmakologisk akseptable salter derav | |
| JPH04225917A (ja) | 記憶増強剤として有用な５−アリ−ル−４−アルキル−３ｈ−１，２，４−トリアゾール−３−チオン類 | |
| NO851113L (no) | ((pyridinyl)-2-pyrimidinyl)ureaforbindelser egnet som kardiotoniske midler og fremgangsmaate for deres fremstilling | |
| NO165542B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive 5-aryl-2,4-dialkyl-3h-1,2,4-triazol-3-thioner. | |
| NO166530B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive piperazin-1,4-naftalendion-derivater. | |
| US4440769A (en) | 2-(4-Phenylalkanoylpiperazin-1-yl) quinazoline compounds, pharmaceutical compositions and method of producing α1 antagonistic activity | |
| KR100556559B1 (ko) | 2-(4-(4-(4,5-디클로로-2-메틸이미다졸-1-일)부틸)-1-피페라지닐)-5-플루오로피리미딘, 이것의 제조 방법 및 이것의치료적 용도 | |
| JP2005530772A (ja) | アミノ酸類縁体 |