DD142343A5 - Verfahren zur herstellung von 1-oxo-1h-pyrimido eckige klammer auf 6,1-b eckige klammer zu benzthiazolen - Google Patents

Verfahren zur herstellung von 1-oxo-1h-pyrimido eckige klammer auf 6,1-b eckige klammer zu benzthiazolen Download PDF

Info

Publication number: DD142343A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; oxo; pyrimido; iii; compounds
Prior art date: 1978-03-13

Application number

DD79211478A

Other languages

German (de)

English (en)

Inventor

Werner Winter

Herman Hindermayr

Egon Roesch

Androniki Roesch

Otto-Henning Wilhelms

Original Assignee

Boehringer Mannheim Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-03-13

Filing date

1979-03-08

Publication date

1980-06-18

1979-03-08 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1980-06-18 Publication of DD142343A5 publication Critical patent/DD142343A5/de

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CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title claims 2
238000004519 manufacturing process Methods 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 34
-1 alkali metal salts Chemical class 0.000 claims description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
230000002378 acidificating effect Effects 0.000 claims description 10
150000001735 carboxylic acids Chemical class 0.000 claims description 10
239000000543 intermediate Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
230000018044 dehydration Effects 0.000 claims description 2
238000006297 dehydration reaction Methods 0.000 claims description 2
230000008030 elimination Effects 0.000 claims description 2
238000003379 elimination reaction Methods 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
230000003301 hydrolyzing effect Effects 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000001819 mass spectrum Methods 0.000 description 18
239000000243 solution Substances 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
239000000203 mixture Substances 0.000 description 10
239000002244 precipitate Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000002211 ultraviolet spectrum Methods 0.000 description 8
XBFRQODQXBMILB-UHFFFAOYSA-N 1,3-benzothiazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1N=CS2 XBFRQODQXBMILB-UHFFFAOYSA-N 0.000 description 7
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 7
JULIITXUIBBZMC-UHFFFAOYSA-N 7-methoxy-1-oxopyrimido[6,1-b][1,3]benzothiazole-4-carboxylic acid Chemical compound C1=NC(=O)N2C3=CC=C(OC)C=C3SC2=C1C(O)=O JULIITXUIBBZMC-UHFFFAOYSA-N 0.000 description 6
238000004108 freeze drying Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000006798 ring closing metathesis reaction Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
MXAAPXJMDOYGCQ-UHFFFAOYSA-N 1,3-benzothiazole-4-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1N=CS2 MXAAPXJMDOYGCQ-UHFFFAOYSA-N 0.000 description 5
XCAZRYIUFHMIDB-UHFFFAOYSA-N 3-(4-methoxy-2-sulfanylphenyl)-2,4-dioxo-1h-pyrimidine-5-carboxylic acid Chemical compound SC1=CC(OC)=CC=C1N1C(=O)C(C(O)=O)=CNC1=O XCAZRYIUFHMIDB-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
230000007017 scission Effects 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 3
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
150000001733 carboxylic acid esters Chemical class 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
AUULTVLMANXTGK-UHFFFAOYSA-N 1-oxopyrimido[6,1-b][1,3]benzothiazole-4-carboxylic acid Chemical compound C1=CC=C2SC3=C(C(=O)O)C=NC(=O)N3C2=C1 AUULTVLMANXTGK-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VIFSARXWHZGSKQ-UHFFFAOYSA-N 7-ethoxy-1-oxopyrimido[6,1-b][1,3]benzothiazole-4-carboxylic acid Chemical compound C1=NC(=O)N2C3=CC=C(OCC)C=C3SC2=C1C(O)=O VIFSARXWHZGSKQ-UHFFFAOYSA-N 0.000 description 2
LKHAOZUQLDJCDW-UHFFFAOYSA-N 8-methoxy-1-oxopyrimido[6,1-b][1,3]benzothiazole-4-carboxylic acid Chemical compound C1=NC(=O)N2C3=CC(OC)=CC=C3SC2=C1C(O)=O LKHAOZUQLDJCDW-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
238000004448 titration Methods 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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 description 1
RWRREZUOSRSYRQ-UHFFFAOYSA-N 1-oxo-n-(2h-tetrazol-5-yl)pyrimido[6,1-b][1,3]benzothiazole-4-carboxamide Chemical compound C1=NC(=O)N2C3=CC=CC=C3SC2=C1C(=O)NC1=NN=NN1 RWRREZUOSRSYRQ-UHFFFAOYSA-N 0.000 description 1
YZXGGQDGOOMVQS-UHFFFAOYSA-N 2,4-dioxo-3-(2-sulfanylphenyl)-1h-pyrimidine-5-carboxylic acid Chemical compound O=C1C(C(=O)O)=CNC(=O)N1C1=CC=CC=C1S YZXGGQDGOOMVQS-UHFFFAOYSA-N 0.000 description 1
JLGLOJZENXRAIR-UHFFFAOYSA-N 2,4-dioxo-3-(6-sulfanyl-1,3-benzodioxol-5-yl)-1h-pyrimidine-5-carboxylic acid Chemical compound O=C1C(C(=O)O)=CNC(=O)N1C(C(=C1)S)=CC2=C1OCO2 JLGLOJZENXRAIR-UHFFFAOYSA-N 0.000 description 1
RXUORKOATDNJFN-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-ylamino)-2-oxoacetic acid Chemical compound C1=CC=C2SC(NC(=O)C(=O)O)=NC2=C1 RXUORKOATDNJFN-UHFFFAOYSA-N 0.000 description 1
YIFCWYUSYGFFMH-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedioic acid Chemical class CCOC=C(C(O)=O)C(O)=O YIFCWYUSYGFFMH-UHFFFAOYSA-N 0.000 description 1
UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 1
OEVSBYUDQXPXTK-UHFFFAOYSA-N 3-(2-sulfanylphenyl)-1h-pyrimidine-2,4-dione Chemical class SC1=CC=CC=C1N1C(=O)NC=CC1=O OEVSBYUDQXPXTK-UHFFFAOYSA-N 0.000 description 1
BUVAEYOJLMJOET-UHFFFAOYSA-N 3-(4,5-dimethoxy-2-sulfanylphenyl)-2,4-dioxo-1h-pyrimidine-5-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC(S)=C1N1C(=O)C(C(O)=O)=CNC1=O BUVAEYOJLMJOET-UHFFFAOYSA-N 0.000 description 1
JCODIGYXTVSARL-UHFFFAOYSA-N 3-(4,5-dimethyl-2-sulfanylphenyl)-2,4-dioxo-1h-pyrimidine-5-carboxylic acid Chemical compound C1=C(C)C(C)=CC(S)=C1N1C(=O)C(C(O)=O)=CNC1=O JCODIGYXTVSARL-UHFFFAOYSA-N 0.000 description 1
WWLZXBYPHFETRT-UHFFFAOYSA-N 3-(4-chloro-2-sulfanylphenyl)-2,4-dioxo-1h-pyrimidine-5-carboxylic acid Chemical compound O=C1C(C(=O)O)=CNC(=O)N1C1=CC=C(Cl)C=C1S WWLZXBYPHFETRT-UHFFFAOYSA-N 0.000 description 1
QZCFSEUUXMOFGX-UHFFFAOYSA-N 3-(4-ethoxy-2-sulfanylphenyl)-2,4-dioxo-1h-pyrimidine-5-carboxylic acid Chemical compound SC1=CC(OCC)=CC=C1N1C(=O)C(C(O)=O)=CNC1=O QZCFSEUUXMOFGX-UHFFFAOYSA-N 0.000 description 1
MWDCWIRINYVFIX-UHFFFAOYSA-N 3-(4-methoxy-3,5-dimethyl-2-sulfanylphenyl)-2,4-dioxo-1h-pyrimidine-5-carboxylic acid Chemical compound SC1=C(C)C(OC)=C(C)C=C1N1C(=O)C(C(O)=O)=CNC1=O MWDCWIRINYVFIX-UHFFFAOYSA-N 0.000 description 1
RWVLSUFUYXWYKA-UHFFFAOYSA-N 4h-pyrimido[2,1-b][1,3]benzothiazole Chemical class C1=CC=C2N3CC=CN=C3SC2=C1 RWVLSUFUYXWYKA-UHFFFAOYSA-N 0.000 description 1
OJMSGHASNINSQX-UHFFFAOYSA-N 7,8-dimethyl-1-oxopyrimido[6,1-b][1,3]benzothiazole-4-carboxylic acid Chemical compound S1C2=C(C(O)=O)C=NC(=O)N2C2=C1C=C(C)C(C)=C2 OJMSGHASNINSQX-UHFFFAOYSA-N 0.000 description 1
FYNXQKIEZHREPQ-UHFFFAOYSA-N 7-chloro-1-oxo-n-(2h-tetrazol-5-yl)pyrimido[6,1-b][1,3]benzothiazole-4-carboxamide Chemical compound C=1C(Cl)=CC=C(N2C(=O)N=C3)C=1SC2=C3C(=O)NC1=NN=NN1 FYNXQKIEZHREPQ-UHFFFAOYSA-N 0.000 description 1
XQISDIUYKSITRN-UHFFFAOYSA-N 7-ethoxy-1-oxo-n-(2h-tetrazol-5-yl)pyrimido[6,1-b][1,3]benzothiazole-4-carboxamide Chemical compound C=1C(OCC)=CC=C(N2C(=O)N=C3)C=1SC2=C3C(=O)NC1=NN=NN1 XQISDIUYKSITRN-UHFFFAOYSA-N 0.000 description 1
HCEQKYVRKNUUAK-UHFFFAOYSA-N 7-methoxy-1-oxo-n-(2h-tetrazol-5-yl)pyrimido[6,1-b][1,3]benzothiazole-4-carboxamide Chemical compound C=1C(OC)=CC=C(N2C(=O)N=C3)C=1SC2=C3C(=O)NC=1N=NNN=1 HCEQKYVRKNUUAK-UHFFFAOYSA-N 0.000 description 1
KTALEGNOFKVCSD-UHFFFAOYSA-N 7-tert-butyl-1-oxopyrimido[6,1-b][1,3]benzothiazole-4-carboxylic acid Chemical compound C1=NC(=O)N2C3=CC=C(C(C)(C)C)C=C3SC2=C1C(O)=O KTALEGNOFKVCSD-UHFFFAOYSA-N 0.000 description 1
GFBHEAVWUCAURZ-UHFFFAOYSA-N 8-nitro-1-oxopyrimido[6,1-b][1,3]benzothiazole-4-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=C2N3C(=O)N=CC(C(=O)O)=C3SC2=C1 GFBHEAVWUCAURZ-UHFFFAOYSA-N 0.000 description 1
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239000004698 Polyethylene Substances 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
LVZGQWKTUCVPBQ-UHFFFAOYSA-N acetic acid;trifluoroborane Chemical compound CC(O)=O.FB(F)F LVZGQWKTUCVPBQ-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
201000009961 allergic asthma Diseases 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
239000000908 ammonium hydroxide Substances 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
OGEDFUAEXRHTEK-UHFFFAOYSA-N ethyl 4-oxo-8-propan-2-ylpyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC(C(C)C)=CC=C2N2C1=NC=C(C(=O)OCC)C2=O OGEDFUAEXRHTEK-UHFFFAOYSA-N 0.000 description 1
HVZLVFBMKGKHMG-UHFFFAOYSA-N ethyl 7,8-dimethoxy-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC(OC)=C(OC)C=C2N2C1=NC=C(C(=O)OCC)C2=O HVZLVFBMKGKHMG-UHFFFAOYSA-N 0.000 description 1
DHZXOOWBIVCEBY-UHFFFAOYSA-N ethyl 7,8-dimethyl-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC(C)=C(C)C=C2N2C1=NC=C(C(=O)OCC)C2=O DHZXOOWBIVCEBY-UHFFFAOYSA-N 0.000 description 1
KAPCIIFJGXKVBW-UHFFFAOYSA-N ethyl 7-methoxy-1-oxopyrimido[6,1-b][1,3]benzothiazole-4-carboxylate Chemical compound C1=C(OC)C=C2SC3=C(C(=O)OCC)C=NC(=O)N3C2=C1 KAPCIIFJGXKVBW-UHFFFAOYSA-N 0.000 description 1
UGVVKBSBLNHFLA-UHFFFAOYSA-N ethyl 8-chloro-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC(Cl)=CC=C2N2C1=NC=C(C(=O)OCC)C2=O UGVVKBSBLNHFLA-UHFFFAOYSA-N 0.000 description 1
GUKMAZONOXKVCI-UHFFFAOYSA-N ethyl 8-ethoxy-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC(OCC)=CC=C2N2C1=NC=C(C(=O)OCC)C2=O GUKMAZONOXKVCI-UHFFFAOYSA-N 0.000 description 1
OLQIQQAUNMPTBM-UHFFFAOYSA-N ethyl 8-methoxy-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC(OC)=CC=C2N2C1=NC=C(C(=O)OCC)C2=O OLQIQQAUNMPTBM-UHFFFAOYSA-N 0.000 description 1
WZXOSTDQIRZRHA-UHFFFAOYSA-N ethyl 8-methyl-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC(C)=CC=C2N2C1=NC=C(C(=O)OCC)C2=O WZXOSTDQIRZRHA-UHFFFAOYSA-N 0.000 description 1
QXYMLLAJEXLARW-UHFFFAOYSA-N ethyl 8-methylsulfanyl-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound S1C2=CC(SC)=CC=C2N2C1=NC=C(C(=O)OCC)C2=O QXYMLLAJEXLARW-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
KIHCIGWIUMZNSI-UHFFFAOYSA-N methyl 8-methoxy-7,9-dimethyl-4-oxopyrimido[2,1-b][1,3]benzothiazole-3-carboxylate Chemical compound COC(=O)C1=CN=C2SC3=C(N2C1=O)C=C(C(=C3C)OC)C KIHCIGWIUMZNSI-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000008512 pyrimidinediones Chemical class 0.000 description 1
AAYNGPDGJLZBOU-UHFFFAOYSA-N pyrimido[2,1-b][1,3]benzothiazol-4-one Chemical class C1=CC=C2N3C(=O)C=CN=C3SC2=C1 AAYNGPDGJLZBOU-UHFFFAOYSA-N 0.000 description 1
WWMJOPAYPOVXQN-UHFFFAOYSA-N pyrimido[6,1-b][1,3]benzothiazol-1-one Chemical compound C1=CC=C2N3C(=O)N=CC=C3SC2=C1 WWMJOPAYPOVXQN-UHFFFAOYSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ZXYAAVBXHKCJJB-UHFFFAOYSA-N uracil-5-carboxylic acid Chemical compound OC(=O)C1=CNC(=O)NC1=O ZXYAAVBXHKCJJB-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD79211478A 1978-03-13 1979-03-08 Verfahren zur herstellung von 1-oxo-1h-pyrimido eckige klammer auf 6,1-b eckige klammer zu benzthiazolen DD142343A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782810863 DE2810863A1 (de)	1978-03-13	1978-03-13	1-oxo-1h-pyrimido eckige klammer auf 6,1-b eckige klammer zu benzthiazol-derivate und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
DD142343A5 true DD142343A5 (de)	1980-06-18

Family

ID=6034315

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79211478A DD142343A5 (de)	1978-03-13	1979-03-08	Verfahren zur herstellung von 1-oxo-1h-pyrimido eckige klammer auf 6,1-b eckige klammer zu benzthiazolen

Country Status (13)

Country	Link
US (1)	US4232024A (da)
EP (1)	EP0005154B1 (da)
JP (1)	JPS54122282A (da)
AT (1)	AT372965B (da)
AU (1)	AU4486379A (da)
CA (1)	CA1103666A (da)
DD (1)	DD142343A5 (da)
DE (2)	DE2810863A1 (da)
DK (1)	DK96579A (da)
ES (1)	ES478485A1 (da)
FI (1)	FI790831A7 (da)
IL (1)	IL56808A0 (da)
ZA (1)	ZA791053B (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4474792A (en) *	1979-06-18	1984-10-02	Riker Laboratories, Inc.	N-Tetrazolyl benzamides and anti-allergic use thereof
US4432986A (en) *	1979-06-18	1984-02-21	Riker Laboratories, Inc.	Tetrazoles bonded to certain polycyclic aromatic systems and anti-allergic use thereof
DK151811C (da) *	1979-11-23	1988-06-06	Pfizer	Analogifremgangsmaade til fremstilling af n-(5-tetrazolyl)-1-oxo-1h-thiazolooe3,2-aaa-pyrimidin-2-carboxamider eller farmaceutisk acceptable kationsalte deraf samt 1-oxo-1h-thiazolooe3,2-aaapyrimidin-2-carboxylsyrer til anvendelse som udgangsmaterialer ved fremgangsmaaden
US4535081A (en) *	1979-11-23	1985-08-13	Pfizer Inc.	Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor
US4377579A (en) *	1981-12-03	1983-03-22	Minnesota Mining And Manufacturing Company	N-(Tetrazol-5-yl)phenazine-1-carboxamides
US4507477A (en) *	1982-09-09	1985-03-26	Riker Laboratories, Inc.	Process for tetrazolyl-pyrimidinone derivatives
GB8403739D0 (en) *	1984-02-13	1984-03-14	Roussel Lab Ltd	Chemical compounds
GB8519261D0 (en) *	1985-07-31	1985-09-04	Roussel Lab Ltd	Chemical compounds
US4762840A (en) *	1984-02-13	1988-08-09	Roussel Uclaf	Pyrimido[2,1-b]benzothiazoles having antiallergic activity
JPS6357522A (ja) *	1986-08-28	1988-03-12	Mect Corp	ピリミド〔２，１−ｄ〕ベンゾチアゾ−ル誘導体からなる血小板凝集抑制剤

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH491944A (de) *	1966-11-29	1970-06-15	Ciba Geigy	Verfahren zur Herstellung von benzheterocyclischen Verbindungen
DE2126148A1 (en)	1971-05-26	1972-12-07	Farbenfabriken Bayer Ag, 5090 Leverkusen	Prepn of uracil derivs - useful as plant - protection agents and their inters
US4041163A (en) *	1976-03-29	1977-08-09	Pfizer Inc.	N-(5-Tetrazolyl)-4-oxo-4H-pyrimido(2,1-b)benzothiazole-3-carboxamide antiallergy agents

1978
- 1978-03-13 DE DE19782810863 patent/DE2810863A1/de not_active Withdrawn
1979
- 1979-02-26 US US06/015,372 patent/US4232024A/en not_active Expired - Lifetime
- 1979-03-06 IL IL56808A patent/IL56808A0/xx unknown
- 1979-03-06 AU AU44863/79A patent/AU4486379A/en not_active Abandoned
- 1979-03-06 CA CA322,968A patent/CA1103666A/en not_active Expired
- 1979-03-07 DE DE7979100676T patent/DE2961394D1/de not_active Expired
- 1979-03-07 JP JP2570279A patent/JPS54122282A/ja active Pending
- 1979-03-07 EP EP79100676A patent/EP0005154B1/de not_active Expired
- 1979-03-07 ZA ZA791053A patent/ZA791053B/xx unknown
- 1979-03-08 DD DD79211478A patent/DD142343A5/de unknown
- 1979-03-08 DK DK96579A patent/DK96579A/da unknown
- 1979-03-09 ES ES478485A patent/ES478485A1/es not_active Expired
- 1979-03-12 AT AT0183279A patent/AT372965B/de not_active IP Right Cessation
- 1979-03-12 FI FI790831A patent/FI790831A7/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA1103666A (en)	1981-06-23
EP0005154B1 (de)	1981-11-25
DK96579A (da)	1979-09-14
AT372965B (de)	1983-12-12
ES478485A1 (es)	1979-11-01
AU4486379A (en)	1979-09-20
ATA183279A (de)	1983-04-15
JPS54122282A (en)	1979-09-21
FI790831A7 (fi)	1979-09-14
DE2961394D1 (en)	1982-01-28
DE2810863A1 (de)	1979-09-27
EP0005154A1 (de)	1979-11-14
IL56808A0 (en)	1979-05-31
US4232024A (en)	1980-11-04
ZA791053B (en)	1980-04-30

Publication	Publication Date	Title
DE69304243T2 (de)	1997-03-06	Chinolin-Verbindungen als Angiotensin-II-Antagoniste
EP0043535B1 (de)	1984-10-31	Tricyclische Arylether, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE2827566A1 (de)	1980-01-10	1,2-dihydro-chinolin-2-on-derivate und verfahren zu ihrer herstellung
EP0011142B1 (de)	1982-12-29	Pyrido (2,1-b) chinazolinon-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
DD143906A5 (de)	1980-09-17	Trianzin-derivate
DE2334266A1 (de)	1974-01-31	Pyrido eckige klammer auf 2,3-d eckige klammer zu pyrimidin-2,4 (1h, 3h)-dione
EP0005154B1 (de)	1981-11-25	1-Oxo-1H-pyrimido (6,1-b) benzthiazol-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
CH626073A5 (da)	1981-10-30
DE2656468A1 (de)	1978-06-15	N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung
EP0251308B1 (de)	1990-11-22	4-Chinolon-3-carbonsäurederivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE2356903A1 (de)	1974-09-05	Verfahren zur herstellung substituierter chromon-3-carbonitrile, -carboxamide und -carbonsaeuren
AT371461B (de)	1983-06-27	Verfahren zur herstellung neuer benzopyranderivate und deren salze
DE3346575A1 (de)	1985-07-04	Neue benzimidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel
DE3320102C2 (da)	1992-07-02
EP0012925B1 (de)	1982-11-10	Neue Chinoloncarbonsäure-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate
CH653036A5 (de)	1985-12-13	Substituierte thiazolo-(3,2-a)-pyrimidine.
DE3117389A1 (de)	1982-11-18	Benzopyranylether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
DE2521980A1 (de)	1975-12-18	1h-tetrazol-derivate
DE2300009A1 (de)	1973-07-12	Verfahren zur herstellung neuer cephalosporinderivate sowie die erhaltenen produkte
EP0576906A1 (de)	1994-01-05	Neue Thienothiazinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antiinflammatorium und Analgeticum
DE3129718C2 (da)	1988-08-18
DE3785987T2 (de)	1993-11-04	Imidazol-derivate und deren salze, verfahren zu deren herstellung, deren anwendung als arzneimittel und deren zusammensetzungen.
DE2742708A1 (de)	1978-05-03	8-(1h-tetrazol-5-yl)-11h-pyrido eckige klammer auf 2,1-b eckige klammer zu chinazolin-11-one und verwendung derselben bei der bekaempfung von bronchialasthma
DE2914218C2 (de)	1985-10-24	N-Acylderivate des Ampicillins und Amoxicillins, Verfahren zu deren Herstellung und pharmazeutische Zubereitungen, welche die Verbindungen enthalten
DE2521326A1 (de)	1975-11-27	Neue thienodiazepinderivate, verfahren zur herstellung derselben und diese enthaltende pharmazeutische mittel