DE2760385C2 - - Google Patents
Info
- Publication number
- DE2760385C2 DE2760385C2 DE19772760385 DE2760385A DE2760385C2 DE 2760385 C2 DE2760385 C2 DE 2760385C2 DE 19772760385 DE19772760385 DE 19772760385 DE 2760385 A DE2760385 A DE 2760385A DE 2760385 C2 DE2760385 C2 DE 2760385C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- ethyl
- formula
- carboxylate
- nmr
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- -1 C1-C4 alkyl radical Chemical class 0.000 description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 11
- 239000000155 melt Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 8
- 239000005695 Ammonium acetate Substances 0.000 description 8
- 229940043376 ammonium acetate Drugs 0.000 description 8
- 235000019257 ammonium acetate Nutrition 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- OHMLBZKIUZTEOC-UHFFFAOYSA-N 2-aminothiophene-3-carboxylic acid Chemical class NC=1SC=CC=1C(O)=O OHMLBZKIUZTEOC-UHFFFAOYSA-N 0.000 description 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000004893 oxazines Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- WHZIZZOTISTHCT-UHFFFAOYSA-N 2-aminothiophene-3-carboxamide Chemical class NC(=O)C=1C=CSC=1N WHZIZZOTISTHCT-UHFFFAOYSA-N 0.000 description 2
- YOPDNLMMBBVYOX-UHFFFAOYSA-N 2-carbamoylthiophene-3-carboxylic acid Chemical compound NC(=O)C=1SC=CC=1C(O)=O YOPDNLMMBBVYOX-UHFFFAOYSA-N 0.000 description 2
- JEDVKUHCDPPWNR-UHFFFAOYSA-N 3h-thieno[2,3-d]pyrimidin-4-one Chemical compound O=C1NC=NC2=C1C=CS2 JEDVKUHCDPPWNR-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- JSLISSGEILAIOU-UHFFFAOYSA-N (4-chloro-2-iodophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C=C1I JSLISSGEILAIOU-UHFFFAOYSA-N 0.000 description 1
- LSAWMHFBOFDZED-UHFFFAOYSA-N 2,4-dihydro-1,3-oxazine-3-carboxylic acid Chemical compound C1C=COCN1C(=O)O LSAWMHFBOFDZED-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- WYOLDVOOOYZSJM-UHFFFAOYSA-N 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound C1CCCC2=C1SC(N)=C2C(O)=O WYOLDVOOOYZSJM-UHFFFAOYSA-N 0.000 description 1
- DYGUSLXLJPITHO-UHFFFAOYSA-N 2-amino-4,5,6,7-tetrahydro-2h-cyclohepta[b]thiophene-3-carboxylic acid Chemical compound C1CCCC2=C(C(O)=O)C(N)SC2=C1 DYGUSLXLJPITHO-UHFFFAOYSA-N 0.000 description 1
- VACNXQPXNNLDIT-UHFFFAOYSA-N 2-amino-4,5-dihydro-2h-cyclopenta[b]thiophene-3-carboxylic acid Chemical compound C1CC2=C(C(O)=O)C(N)SC2=C1 VACNXQPXNNLDIT-UHFFFAOYSA-N 0.000 description 1
- RHJAOEKFHFTYKS-UHFFFAOYSA-N 2-amino-4-methyl-5-octylthiophene-3-carboxylic acid;hydrate Chemical compound O.CCCCCCCCC=1SC(N)=C(C(O)=O)C=1C RHJAOEKFHFTYKS-UHFFFAOYSA-N 0.000 description 1
- IAUQUGBWARPCRD-UHFFFAOYSA-N 2-amino-5-butylthiophene-3-carboxylic acid Chemical compound CCCCC1=CC(C(O)=O)=C(N)S1 IAUQUGBWARPCRD-UHFFFAOYSA-N 0.000 description 1
- VRNVWBPFCCUXMB-UHFFFAOYSA-N 2-amino-5-hexylthiophene-3-carboxylic acid Chemical compound CCCCCCC1=CC(C(O)=O)=C(N)S1 VRNVWBPFCCUXMB-UHFFFAOYSA-N 0.000 description 1
- NYHTVTHAYNROCN-UHFFFAOYSA-N 2-amino-5-pentylthiophene-3-carboxylic acid Chemical compound CCCCCC1=CC(C(O)=O)=C(N)S1 NYHTVTHAYNROCN-UHFFFAOYSA-N 0.000 description 1
- ASHBREDDKSMEBB-UHFFFAOYSA-N 2-amino-5-propan-2-ylthiophene-3-carboxylic acid Chemical compound CC(C)C1=CC(C(O)=O)=C(N)S1 ASHBREDDKSMEBB-UHFFFAOYSA-N 0.000 description 1
- DSDPWTCPFZHYRR-UHFFFAOYSA-N 2-amino-5-propylthiophene-3-carboxylic acid Chemical compound CCCC1=CC(C(O)=O)=C(N)S1 DSDPWTCPFZHYRR-UHFFFAOYSA-N 0.000 description 1
- JSFDJOIURTZKJF-UHFFFAOYSA-N 2H-thieno[2,3-d][1,3]oxazine-2-carboxylic acid Chemical compound C1=CSC2=NC(OC=C21)C(=O)O JSFDJOIURTZKJF-UHFFFAOYSA-N 0.000 description 1
- WVPWIAJQKYPRFM-UHFFFAOYSA-N 2h-1,3-oxazine-2-carboxylic acid Chemical compound OC(=O)C1OC=CC=N1 WVPWIAJQKYPRFM-UHFFFAOYSA-N 0.000 description 1
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical compound NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 description 1
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- FOAMHWUDGOAJCW-UHFFFAOYSA-N 6-ethyl-3-methyl-4-oxothieno[2,3-d]pyrimidine-2-carboxylic acid Chemical compound S1C(CC)=CC2=C1N=C(C(O)=O)N(C)C2=O FOAMHWUDGOAJCW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 208000004262 Food Hypersensitivity Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PYNLNQLSVWQNLT-BQYQJAHWSA-N O=C1C2=C(N=C(O1)/C=C/C(=O)OCC)SC1=C2CCCC1 Chemical compound O=C1C2=C(N=C(O1)/C=C/C(=O)OCC)SC1=C2CCCC1 PYNLNQLSVWQNLT-BQYQJAHWSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- TUJLSKHVJKNTNA-UHFFFAOYSA-N [K].[K].N1=C(C(O)=O)NC(=O)C2=C1SC(CC(C)C)=C2C Chemical compound [K].[K].N1=C(C(O)=O)NC(=O)C2=C1SC(CC(C)C)=C2C TUJLSKHVJKNTNA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- GJYJYFHBOBUTBY-UHFFFAOYSA-N alpha-camphorene Chemical compound CC(C)=CCCC(=C)C1CCC(CCC=C(C)C)=CC1 GJYJYFHBOBUTBY-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 229940039409 ammonium valerate Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- WWLOCCUNZXBJFR-UHFFFAOYSA-N azanium;benzenesulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C1=CC=CC=C1 WWLOCCUNZXBJFR-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- GYHYNHGCEZOENP-UHFFFAOYSA-N butyl 6-ethyl-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound O=C1NC(C(=O)OCCCC)=NC2=C1C=C(CC)S2 GYHYNHGCEZOENP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- HRXDYOKVWGTDPD-UHFFFAOYSA-N ctk4b9193 Chemical compound [NH4+].[O-]S(F)(=O)=O HRXDYOKVWGTDPD-UHFFFAOYSA-N 0.000 description 1
- 150000001925 cycloalkenes Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- WEGTVVQUVCDZJI-UHFFFAOYSA-N ethyl 4-oxo-6-pentyl-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound S1C(CCCCC)=CC2=C1N=C(C(=O)OCC)NC2=O WEGTVVQUVCDZJI-UHFFFAOYSA-N 0.000 description 1
- CRSLIQOJAFZVDE-UHFFFAOYSA-N ethyl 4-oxo-6-pentylthieno[2,3-d][1,3]oxazine-2-carboxylate Chemical compound S1C(CCCCC)=CC2=C1N=C(C(=O)OCC)OC2=O CRSLIQOJAFZVDE-UHFFFAOYSA-N 0.000 description 1
- WSBSNMSWIFSZCH-UHFFFAOYSA-N ethyl 4-oxo-6-propan-2-yl-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound O=C1NC(C(=O)OCC)=NC2=C1C=C(C(C)C)S2 WSBSNMSWIFSZCH-UHFFFAOYSA-N 0.000 description 1
- PFROOWCYRQFRQO-UHFFFAOYSA-N ethyl 4-oxo-6-propan-2-ylthieno[2,3-d][1,3]oxazine-2-carboxylate Chemical compound O=C1OC(C(=O)OCC)=NC2=C1C=C(C(C)C)S2 PFROOWCYRQFRQO-UHFFFAOYSA-N 0.000 description 1
- GIORZHVDKLWIGT-UHFFFAOYSA-N ethyl 4-oxo-6-propyl-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound S1C(CCC)=CC2=C1N=C(C(=O)OCC)NC2=O GIORZHVDKLWIGT-UHFFFAOYSA-N 0.000 description 1
- CZGIHKHWXWROCY-UHFFFAOYSA-N ethyl 4-oxo-6-propylthieno[2,3-d][1,3]oxazine-2-carboxylate Chemical compound S1C(CCC)=CC2=C1N=C(C(=O)OCC)OC2=O CZGIHKHWXWROCY-UHFFFAOYSA-N 0.000 description 1
- LVLHXJIIBCEPDC-UHFFFAOYSA-N ethyl 5-amino-6-ethyl-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound O=C1NC(C(=O)OCC)=NC2=C1C(N)=C(CC)S2 LVLHXJIIBCEPDC-UHFFFAOYSA-N 0.000 description 1
- COPPXSKHTAHKTA-UHFFFAOYSA-N ethyl 5-methyl-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound O=C1NC(C(=O)OCC)=NC2=C1C(C)=CS2 COPPXSKHTAHKTA-UHFFFAOYSA-N 0.000 description 1
- GXBZAFTWKIGADP-UHFFFAOYSA-N ethyl 5-methyl-6-octyl-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound N1=C(C(=O)OCC)NC(=O)C2=C1SC(CCCCCCCC)=C2C GXBZAFTWKIGADP-UHFFFAOYSA-N 0.000 description 1
- LNYABNLPMYMQEX-UHFFFAOYSA-N ethyl 5-methyl-6-octyl-4-oxothieno[2,3-d][1,3]oxazine-2-carboxylate Chemical compound N1=C(C(=O)OCC)OC(=O)C2=C1SC(CCCCCCCC)=C2C LNYABNLPMYMQEX-UHFFFAOYSA-N 0.000 description 1
- HRPLQSTZJUFFHT-UHFFFAOYSA-N ethyl 6-amino-5-methyl-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound O=C1NC(C(=O)OCC)=NC2=C1C(C)=C(N)S2 HRPLQSTZJUFFHT-UHFFFAOYSA-N 0.000 description 1
- FHLGOJYYHWICHD-UHFFFAOYSA-N ethyl 6-butyl-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound S1C(CCCC)=CC2=C1N=C(C(=O)OCC)NC2=O FHLGOJYYHWICHD-UHFFFAOYSA-N 0.000 description 1
- PXXHQUIHNRJLLN-UHFFFAOYSA-N ethyl 6-butyl-4-oxothieno[2,3-d][1,3]oxazine-2-carboxylate Chemical compound S1C(CCCC)=CC2=C1N=C(C(=O)OCC)OC2=O PXXHQUIHNRJLLN-UHFFFAOYSA-N 0.000 description 1
- QPZFOQTXJZNYFF-UHFFFAOYSA-N ethyl 6-ethyl-5-iodo-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound O=C1NC(C(=O)OCC)=NC2=C1C(I)=C(CC)S2 QPZFOQTXJZNYFF-UHFFFAOYSA-N 0.000 description 1
- ROZJOOYWKULKPX-UHFFFAOYSA-N ethyl 6-hexyl-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound S1C(CCCCCC)=CC2=C1N=C(C(=O)OCC)NC2=O ROZJOOYWKULKPX-UHFFFAOYSA-N 0.000 description 1
- QZIWKVPANDVSQC-UHFFFAOYSA-N ethyl 6-methyl-4-oxo-3h-thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound O=C1NC(C(=O)OCC)=NC2=C1C=C(C)S2 QZIWKVPANDVSQC-UHFFFAOYSA-N 0.000 description 1
- WKVOPTRCXUPDNL-UHFFFAOYSA-N ethyl 6-methyl-4-oxothieno[2,3-d][1,3]oxazine-2-carboxylate Chemical compound O=C1OC(C(=O)OCC)=NC2=C1C=C(C)S2 WKVOPTRCXUPDNL-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000020932 food allergy Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- HAYRJNOYGFRPKW-UHFFFAOYSA-M sodium;6-ethyl-3-methyl-4-oxothieno[2,3-d]pyrimidine-2-carboxylate Chemical compound [Na+].S1C(CC)=CC2=C1N=C(C([O-])=O)N(C)C2=O HAYRJNOYGFRPKW-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- NIYGIWBXQHELDN-UHFFFAOYSA-N thieno[2,3-d]pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C2C=CSC2=N1 NIYGIWBXQHELDN-UHFFFAOYSA-N 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772760385 DE2760385C2 (enrdf_load_stackoverflow) | 1977-10-18 | 1977-10-18 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772760385 DE2760385C2 (enrdf_load_stackoverflow) | 1977-10-18 | 1977-10-18 | |
| DE19772746750 DE2746750A1 (de) | 1977-10-18 | 1977-10-18 | Antiallergische verbindungen, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2760385C2 true DE2760385C2 (enrdf_load_stackoverflow) | 1991-06-13 |
Family
ID=25772920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772760385 Expired - Fee Related DE2760385C2 (enrdf_load_stackoverflow) | 1977-10-18 | 1977-10-18 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2760385C2 (enrdf_load_stackoverflow) |
-
1977
- 1977-10-18 DE DE19772760385 patent/DE2760385C2/de not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69530989T2 (de) | Neue pyrimidinderivate und verfahren zu ihrer herstellung | |
| DE69025723T2 (de) | N-(Pyrrolo(2-3-d)pyrimidin-3-ylacyl)-Glutaminsäurederivate | |
| DE69322033T2 (de) | Kondensierte Pyridin Derivate als Hemmer von Effekten freier Radikaler | |
| DE3001328C2 (enrdf_load_stackoverflow) | ||
| CH381706A (de) | Verfahren zur Herstellung von Sulfamylanthranilsäuren | |
| DD296927A5 (de) | Verfahren zur herstellung von 4(3h)-pteridinonen | |
| DE3533331A1 (de) | Pyridothiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2424334A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| EP0005154B1 (de) | 1-Oxo-1H-pyrimido (6,1-b) benzthiazol-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
| WO1997037977A1 (de) | Substituierte-chinolin-derivate mit antiviraler wirkung | |
| DE2760385C2 (enrdf_load_stackoverflow) | ||
| CH647777A5 (de) | Substituierte pyrido-(1,2-a)-pyrimidine. | |
| DE1966640A1 (de) | Verfahren zur herstellung von 4- und/ oder 4,6-substituierten pyrazolo (3,4-d)pyrimidinen | |
| EP0088250B1 (de) | Neue basisch substituierte 4-Phenyl-4,5,6,7-tetrahydrothieno-(2,3-c)pyridine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| SU1048986A3 (ru) | Способ получени 3-замещенных тетрагидропирроло/1,2- @ / пиримидинов,их кислотно-аддитивных или четвертичных солей | |
| DE3785076T2 (de) | Pyrido(4,3-d)pyrimidin-derivate. | |
| DE3017977A1 (de) | Neue substituierte 2(3h)-benzothiazolone | |
| DE2746750C2 (enrdf_load_stackoverflow) | ||
| DE3129718C2 (enrdf_load_stackoverflow) | ||
| DE2914218C2 (de) | N-Acylderivate des Ampicillins und Amoxicillins, Verfahren zu deren Herstellung und pharmazeutische Zubereitungen, welche die Verbindungen enthalten | |
| DE2760384C2 (enrdf_load_stackoverflow) | ||
| DD140253A5 (de) | Verfahren zur herstellung von 2,6-bis-(aminoacylamino)-benzo-eckige klammer auf 1,2-d:5,4-d'eckige klammer zu-bisthiazolen und 2-amino-6-(aminoacylamino)-benzo-eckige klammer auf 1,2-d:5,4-d'eckige klammer zu-bisthiazolen | |
| DE3447730A1 (de) | Pyrazolopyridinderivate | |
| DD237660A5 (de) | Verfahren zur herstellung von purinderivaten | |
| CH660011A5 (de) | Substituierte carboxy-thiazolo-(3,2-a)-pyrimidin-derivate. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| Q172 | Divided out of (supplement): |
Ref country code: DE Ref document number: 2746750 |
|
| 8110 | Request for examination paragraph 44 | ||
| AC | Divided out of |
Ref country code: DE Ref document number: 2746750 Format of ref document f/p: P |
|
| 8127 | New person/name/address of the applicant |
Owner name: BRISTOL-MYERS SQUIBB CO. (N.D.GES.D.STAATES DELAWA |
|
| 8128 | New person/name/address of the agent |
Representative=s name: KINZEBACH, W., DIPL.-CHEM. DR.PHIL. RIEDL, P., DIP |
|
| AC | Divided out of |
Ref country code: DE Ref document number: 2746750 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |