DD281600A5 - Herstellung von oxophthalazinyl-essigsaeuren mit benzothiazol- oder anderen heterocyclischen seitenketten - Google Patents

Herstellung von oxophthalazinyl-essigsaeuren mit benzothiazol- oder anderen heterocyclischen seitenketten Download PDF

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Publication number: DD281600A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; hydrogen; alkyl; acid
Prior art date: 1987-06-09

Application number

DD88316492A

Other languages

German (de)

English (en)

Inventor

Banavara L Mylari

William J Zembrowski

Original Assignee

��@��Kk��

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.)

1987-06-09

Filing date

1988-06-07

Publication date

1990-08-15

1988-06-07 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1990-08-15 Publication of DD281600A5 publication Critical patent/DD281600A5/de

Links

239000002253 acid Substances 0.000 title claims description 34
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title abstract 5
238000002360 preparation method Methods 0.000 title description 6
239000000052 vinegar Substances 0.000 title description 2
235000021419 vinegar Nutrition 0.000 title description 2
150000007513 acids Chemical class 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 25
150000001875 compounds Chemical class 0.000 claims description 88
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 22
239000000460 chlorine Substances 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 15
-1 alkaline earth metal cyanide Chemical class 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000005605 benzo group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 abstract description 4
235000011054 acetic acid Nutrition 0.000 abstract description 3
150000002148 esters Chemical class 0.000 abstract description 3
150000001243 acetic acids Chemical class 0.000 abstract description 2
239000003288 aldose reductase inhibitor Substances 0.000 abstract description 2
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 abstract description 2
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
239000008177 pharmaceutical agent Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 23
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
239000000203 mixture Substances 0.000 description 21
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
238000010992 reflux Methods 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000047 product Substances 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
239000005457 ice water Substances 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
125000002541 furyl group Chemical group 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 3
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
101150052863 THY1 gene Proteins 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
206010007749 Cataract diabetic Diseases 0.000 description 2
206010012689 Diabetic retinopathy Diseases 0.000 description 2
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 2
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000006680 Reformatsky reaction Methods 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
201000007025 diabetic cataract Diseases 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000010936 titanium Substances 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
YXRHEUYEOGNXIY-UHFFFAOYSA-N 2-amino-4,6-difluorobenzenethiol;hydrochloride Chemical compound Cl.NC1=CC(F)=CC(F)=C1S YXRHEUYEOGNXIY-UHFFFAOYSA-N 0.000 description 1
REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
102000016912 Aldehyde Reductase Human genes 0.000 description 1
108010053754 Aldehyde reductase Proteins 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CXFHMSJQWOIZBA-UHFFFAOYSA-N C(C)(=O)OC1=NN(C(C2=CC=CC=C12)=O)CC#N Chemical compound C(C)(=O)OC1=NN(C(C2=CC=CC=C12)=O)CC#N CXFHMSJQWOIZBA-UHFFFAOYSA-N 0.000 description 1
101100243951 Caenorhabditis elegans pie-1 gene Proteins 0.000 description 1
LWEVYOBVVPZDKE-UHFFFAOYSA-N Cl.FC(C=1C=CC=C(C1)S)(F)F Chemical compound Cl.FC(C=1C=CC=C(C1)S)(F)F LWEVYOBVVPZDKE-UHFFFAOYSA-N 0.000 description 1
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
208000032131 Diabetic Neuropathies Diseases 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
240000002989 Euphorbia neriifolia Species 0.000 description 1
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 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000037396 body weight Effects 0.000 description 1
NMEGSGKCIWQRDB-UHFFFAOYSA-N butyl 2-bromoacetate Chemical compound CCCCOC(=O)CBr NMEGSGKCIWQRDB-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
SSOVHFPWMPUQOS-UHFFFAOYSA-N cyanomethyl benzenesulfonate Chemical compound N#CCOS(=O)(=O)C1=CC=CC=C1 SSOVHFPWMPUQOS-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000007171 neuropathology Effects 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
229910052727 yttrium Inorganic materials 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Thiazole And Isothizaole Compounds (AREA)

DD88316492A 1987-06-09 1988-06-07 Herstellung von oxophthalazinyl-essigsaeuren mit benzothiazol- oder anderen heterocyclischen seitenketten DD281600A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US5989987A	1987-06-09	1987-06-09

Publications (1)

Publication Number	Publication Date
DD281600A5 true DD281600A5 (de)	1990-08-15

Family

ID=22026001

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD88316492A DD281600A5 (de)	1987-06-09	1988-06-07	Herstellung von oxophthalazinyl-essigsaeuren mit benzothiazol- oder anderen heterocyclischen seitenketten
DD88326850A DD280323A5 (de)	1987-06-09	1988-06-07	Herstellung von zwischenprodukten der oxophthalazinyl-essigsaeuren mit benzothiazol- oder anderen heterocyclischen seitenketten
DD88326849A DD280320A5 (de)	1987-06-09	1988-06-07	Herstellung von zwischenprodukten der oxophthalazinyl-essigsaeuren mit benzothiazol oder anderen heterocyclischen seitenketten

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD88326850A DD280323A5 (de)	1987-06-09	1988-06-07	Herstellung von zwischenprodukten der oxophthalazinyl-essigsaeuren mit benzothiazol- oder anderen heterocyclischen seitenketten
DD88326849A DD280320A5 (de)	1987-06-09	1988-06-07	Herstellung von zwischenprodukten der oxophthalazinyl-essigsaeuren mit benzothiazol oder anderen heterocyclischen seitenketten

Country Status (26)

Country	Link
EP (1)	EP0295051B1 (fr)
JP (1)	JPH0676391B2 (fr)
KR (1)	KR900004698B1 (fr)
CN (1)	CN1024347C (fr)
AT (1)	ATE90347T1 (fr)
AU (1)	AU593742B2 (fr)
CA (1)	CA1321791C (fr)
CS (1)	CS274628B2 (fr)
DD (3)	DD281600A5 (fr)
DE (1)	DE3881583T2 (fr)
DK (1)	DK309988A (fr)
EG (1)	EG18613A (fr)
ES (1)	ES2040853T3 (fr)
FI (1)	FI93835C (fr)
HU (1)	HU205108B (fr)
IE (1)	IE61499B1 (fr)
IL (1)	IL86660A0 (fr)
MY (1)	MY103573A (fr)
NO (1)	NO176317C (fr)
NZ (1)	NZ224937A (fr)
PH (1)	PH25928A (fr)
PL (1)	PL157690B1 (fr)
PT (1)	PT87669B (fr)
SU (1)	SU1678208A3 (fr)
YU (1)	YU46696B (fr)
ZA (1)	ZA884075B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0322153A3 (fr) *	1987-12-21	1990-08-16	Pfizer Inc.	Acides hétérocyclyl oxophtalazinyl acétiques
WO1989006651A1 (fr) *	1988-01-19	1989-07-27	Pfizer Inc.	Acides 1h-indazole-3-acetiques servant d'inhibiteurs d'aldose reductase
US4904782A (en) *	1988-02-29	1990-02-27	Pfizer Inc.	Process for the production of phthalazineacetic acid ester derivatives and a novel intermediate
US4954629A (en) *	1989-05-11	1990-09-04	Pfizer Inc.	Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof
FR2647676A1 (fr) *	1989-06-05	1990-12-07	Union Pharma Scient Appl	Nouveaux derives de pyridazinone, leurs procedes de preparation, medicaments les contenant, utiles notamment comme inhibiteurs de l'aldose reductase
FI922308A7 (fi) *	1989-12-15	1992-05-21	Pfizer	Substituoituja oksoftalatsinyylietikkahappoja ja niiden anologeja
US5064830A (en) *	1990-08-02	1991-11-12	Pfizer Inc.	Lowering of blood uric acid levels
WO1992003432A1 (fr) *	1990-08-28	1992-03-05	Pfizer Inc.	Monohydrate d'acide 3-(5-trifluoromethylbenzothiazol-2-ylmethyle)-4-oxo-3h-phytalazine-1-ylacetique
WO1992017446A2 (fr) *	1991-03-28	1992-10-15	Pfizer Inc.	Acides acetiques de pyridazinone utilises comme agents inhibiteurs de l'aldose-reductase
FR2682108B1 (fr) *	1991-10-07	1994-01-07	Lipha	Acide 3,4-dihydro-4-oxo-3(prop-2-enyl)-1-phtalazineacetiques et derives, leurs preparations et medicaments les contenant.
EP0652213B1 (fr) *	1993-10-06	1997-08-27	SUMIKA FINE CHEMICALS Co., Ltd.	Procédé de préparation de alkyle 3-phtalidenylideneacetate
US5700819A (en) *	1994-11-29	1997-12-23	Grelan Pharmaceutical Co., Ltd.	2-substituted benzothiazole derivatives and prophylactic and therapeutic agents for the treatment of diabetic complications
IL124236A (en) *	1997-05-05	2003-01-12	Pfizer	Pharmaceutical composition for treating or reversing diabetic cardiomyopathy comprising aldose reductase inhibitor
EP0982306A3 (fr) *	1998-08-21	2000-07-05	Pfizer Products Inc.	Polymorphe du monohydrate de zopolrestat
SG82702A1 (en) *	1999-09-28	2001-08-21	Ebauchesfabrik Eta Ag	Timepiece including a movement mounted in a casing ring
CN116970317B (zh) *	2023-03-20	2024-06-25	安徽庆丰涂料科技有限公司	可呼吸的负离子抗菌涂料及其加工工艺

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE47592B1 (en) *	1977-12-29	1984-05-02	Ici Ltd	Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture
JPS5931509B2 (ja) *	1979-06-06	1984-08-02	昭和電工株式会社	３−ヒドロキシ−３−メチルフタリド又はその核置換体の製造法
DE3684410D1 (de) *	1985-11-07	1992-04-23	Pfizer	Heterocyclische oxophthalazinylessigsaeure.

1988
- 1988-06-02 JP JP63136601A patent/JPH0676391B2/ja not_active Expired - Lifetime
- 1988-06-06 MY MYPI88000606A patent/MY103573A/en unknown
- 1988-06-06 PH PH37013A patent/PH25928A/en unknown
- 1988-06-07 PL PL1988272899A patent/PL157690B1/pl unknown
- 1988-06-07 CA CA000568775A patent/CA1321791C/fr not_active Expired - Fee Related
- 1988-06-07 CS CS392488A patent/CS274628B2/cs not_active IP Right Cessation
- 1988-06-07 AT AT88305180T patent/ATE90347T1/de not_active IP Right Cessation
- 1988-06-07 DD DD88316492A patent/DD281600A5/de not_active IP Right Cessation
- 1988-06-07 ES ES198888305180T patent/ES2040853T3/es not_active Expired - Lifetime
- 1988-06-07 DD DD88326850A patent/DD280323A5/de not_active IP Right Cessation
- 1988-06-07 EP EP88305180A patent/EP0295051B1/fr not_active Expired - Lifetime
- 1988-06-07 DD DD88326849A patent/DD280320A5/de not_active IP Right Cessation
- 1988-06-07 DE DE8888305180T patent/DE3881583T2/de not_active Expired - Fee Related
- 1988-06-08 NO NO882516A patent/NO176317C/no not_active IP Right Cessation
- 1988-06-08 NZ NZ224937A patent/NZ224937A/xx unknown
- 1988-06-08 IL IL86660A patent/IL86660A0/xx not_active IP Right Cessation
- 1988-06-08 PT PT87669A patent/PT87669B/pt not_active IP Right Cessation
- 1988-06-08 KR KR1019880006855A patent/KR900004698B1/ko not_active Expired
- 1988-06-08 IE IE171688A patent/IE61499B1/en unknown
- 1988-06-08 DK DK309988A patent/DK309988A/da not_active Application Discontinuation
- 1988-06-08 AU AU17491/88A patent/AU593742B2/en not_active Ceased
- 1988-06-08 FI FI882722A patent/FI93835C/fi not_active IP Right Cessation
- 1988-06-08 SU SU884355901A patent/SU1678208A3/ru active
- 1988-06-08 CN CN88103507A patent/CN1024347C/zh not_active Expired - Fee Related
- 1988-06-08 YU YU111188A patent/YU46696B/sh unknown
- 1988-06-08 HU HU882971A patent/HU205108B/hu not_active IP Right Cessation
- 1988-06-08 ZA ZA884075A patent/ZA884075B/xx unknown
- 1988-06-09 EG EG320/88A patent/EG18613A/xx active

Also Published As

Publication number	Publication date
AU593742B2 (en)	1990-02-15
NO882516D0 (no)	1988-06-08
DE3881583D1 (de)	1993-07-15
JPS643173A (en)	1989-01-06
DK309988A (da)	1988-12-10
YU46696B (sh)	1994-04-05
IE61499B1 (en)	1994-11-02
ES2040853T3 (es)	1993-11-01
PH25928A (en)	1991-12-19
FI882722A0 (fi)	1988-06-08
CS274628B2 (en)	1991-09-15
AU1749188A (en)	1988-12-15
IE881716L (en)	1988-12-09
EG18613A (en)	1993-08-30
IL86660A0 (en)	1988-11-30
KR900004698B1 (ko)	1990-07-02
NZ224937A (en)	1991-01-29
CN1024347C (zh)	1994-04-27
PT87669B (pt)	1992-09-30
EP0295051A2 (fr)	1988-12-14
CN88103507A (zh)	1988-12-28
DK309988D0 (da)	1988-06-08
MY103573A (en)	1993-08-28
CA1321791C (fr)	1993-08-31
CS392488A2 (en)	1990-08-14
YU111188A (en)	1989-12-31
HU205108B (en)	1992-03-30
NO882516L (no)	1988-12-12
DD280323A5 (de)	1990-07-04
NO176317B (no)	1994-12-05
PL157690B1 (en)	1992-06-30
FI93835C (fi)	1995-06-12
NO176317C (no)	1995-03-15
EP0295051B1 (fr)	1993-06-09
EP0295051A3 (en)	1989-03-22
DE3881583T2 (de)	1993-09-16
DD280320A5 (de)	1990-07-04
FI882722A7 (fi)	1988-12-10
FI93835B (fi)	1995-02-28
JPH0676391B2 (ja)	1994-09-28
ZA884075B (en)	1990-02-28
KR890000476A (ko)	1989-03-14
PT87669A (pt)	1988-07-01
SU1678208A3 (ru)	1991-09-15
ATE90347T1 (de)	1993-06-15
PL272899A1 (en)	1989-07-10

Legal Events

Date	Code	Title	Description
1998-07-02	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD281600A5 (de)	1990-08-15	Herstellung von oxophthalazinyl-essigsaeuren mit benzothiazol- oder anderen heterocyclischen seitenketten
DE3689924T4 (de)	1995-05-11	Durch eine heterocyclische Gruppe substituierte Phenoxyalkylisoxazole und ihre Verwendung als antivirale Mittel.
EP0763036B1 (fr)	2002-09-11	DERIVES DE PYRROLE [a]-ANNELES ET LEUR UTILISATION DANS LE DOMAINE PHARMACEUTIQUE
DE69513332T2 (de)	2000-07-27	(Thia)cycloalkyl(b)indolderivate als 5-lipoxygenase Inhibitoren
DE69432542T2 (de)	2004-03-04	Tetraderivate, ihre Herstellung und Verwendung
DD244133A5 (de)	1987-03-25	Verfahren zur herstellung von substituierten 2-oxindolen als analgetische und entzuendungshemmende mittel
DE69319391T2 (de)	1998-10-29	1,2,4-Oxadiazolyl oder 1,2,4-Thiadiazolyl-Derivate als Angiotensin II Antagonisten
DE2824575C2 (de)	1986-07-03	4-substituierte Methylen-1,3-dithietan-2-carbonsäure oder ihre niederen Alkylester, Verfahren zu ihrer Herstellung und ihre Verwendung als Acylierungsmittel
DE69204920T2 (de)	1996-03-28	Angiotensin-II-Antagoniste.
EP1098891B1 (fr)	2005-08-10	Amines thiazolidin-2-ylidenes polycycliques, leur procede de production et leur utilisation comme medicaments
DE69800699T2 (de)	2001-09-06	Verbindungen
DE10115408A1 (de)	2002-10-02	Benzofuran-Derivate
DE60037766T2 (de)	2009-01-15	Verfahren zur Herstellung von 2-Alkyl-3-aminothiophen Derivaten und 3-Aminothiophen Derivate
EP0350437B1 (fr)	1995-09-06	Phénylhétérocycles disubstitués en 3,4 et leur utilisation
DD295373A5 (de)	1991-10-31	Verfahren zur herstellung von alpha-cyan-beta-oxopropionamiden
FR2496666A1 (fr)	1982-06-25	Nouveaux derives de cephalosporine et composition pharmaceutique les contenant
DE2624344C2 (de)	1987-03-19	Verfahren zur Herstellung von in 1-Stellung unsubstituierten 3-(2-Hydroxyäthyl)-indol-Derivaten
DE2841644A1 (de)	1979-04-05	3(tetrazol-5-yl)-1-azaxanthone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
JP2001515066A (ja)	2001-09-18	置換された２−ニトログアニジン誘導体の製造方法
EP0003360B1 (fr)	1981-12-30	Azathianaphtalènes, procédé pour leur préparation, préparations pharmaceutiques les contenant et leur utilisation
DE69005833T2 (de)	1994-04-28	Entzündungshemmende 1-Heteroaryloxindole-3-Carboxamide.
CH660011A5 (de)	1987-03-13	Substituierte carboxy-thiazolo-(3,2-a)-pyrimidin-derivate.
DE69714076T2 (de)	2003-03-06	Herstellung von thiazolen
EP0562382B1 (fr)	1998-01-21	Procédé de préparation de dérivés d'acides isoxazole-3,4-dicarboxyliques
EP0336886A1 (fr)	1989-10-11	Composés ayant une groupe thio