DD264425A5 - Verfahren zur herstellung neuer benzolsulfonamide-indanylverbindungen - Google Patents

Verfahren zur herstellung neuer benzolsulfonamide-indanylverbindungen Download PDF

Info

Publication number: DD264425A5
Authority: DD; German Democratic Republic
Prior art keywords: group; general formula; indanyl; temperatures; carbon atoms
Prior art date: 1986-07-16

Application number

DD87304898A

Other languages

German (de)

English (en)

Inventor

Josef Nickl

Armin Heckel

Erich Mueller

Berthold Narr

Johannes Weisenberger

Wolfgang Eisert

Thomas Mueller

Original Assignee

��K@��@��@��k��

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.)

1986-07-16

Filing date

1987-07-13

Publication date

1989-02-01

1987-07-13 Application filed by ��K@��@��@��k�� filed Critical ��K@��@��@��k��

1989-02-01 Publication of DD264425A5 publication Critical patent/DD264425A5/de

Links

-1 BENZOLSULPHONAMIDE INDANYL COMPOUNDS Chemical class 0.000 title claims abstract description 95
238000004519 manufacturing process Methods 0.000 title description 7
238000000034 method Methods 0.000 claims abstract description 37
238000002360 preparation method Methods 0.000 claims abstract description 30
230000008569 process Effects 0.000 claims abstract description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 14
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 11
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 11
125000002947 alkylene group Chemical group 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000004450 alkenylene group Chemical group 0.000 claims abstract description 6
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 90
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 64
125000004432 carbon atom Chemical group C* 0.000 claims description 47
230000007062 hydrolysis Effects 0.000 claims description 30
238000006460 hydrolysis reaction Methods 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 25
239000002904 solvent Substances 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 22
239000000460 chlorine Substances 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
238000009835 boiling Methods 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000002585 base Substances 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 13
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
150000007529 inorganic bases Chemical class 0.000 claims description 9
150000007530 organic bases Chemical class 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
238000006114 decarboxylation reaction Methods 0.000 claims description 7
230000001681 protective effect Effects 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
230000032050 esterification Effects 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
230000000269 nucleophilic effect Effects 0.000 claims description 5
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical group OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 4
239000002841 Lewis acid Substances 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
150000007517 lewis acids Chemical class 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
229910052721 tungsten Inorganic materials 0.000 claims description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000012312 sodium hydride Substances 0.000 claims description 3
229910000104 sodium hydride Inorganic materials 0.000 claims description 3
ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 claims description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 claims description 2
239000011592 zinc chloride Substances 0.000 claims description 2
235000005074 zinc chloride Nutrition 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 claims 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
229910015900 BF3 Inorganic materials 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
125000003158 alcohol group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000000837 carbohydrate group Chemical group 0.000 claims 1
239000003245 coal Substances 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
238000002203 pretreatment Methods 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
239000004071 soot Substances 0.000 claims 1
125000001424 substituent group Chemical group 0.000 abstract description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 120
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 100
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 69
238000002844 melting Methods 0.000 description 54
230000008018 melting Effects 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
239000000741 silica gel Substances 0.000 description 42
229910002027 silica gel Inorganic materials 0.000 description 42
229960000583 acetic acid Drugs 0.000 description 35
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
239000003921 oil Substances 0.000 description 28
239000007795 chemical reaction product Substances 0.000 description 25
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
239000012362 glacial acetic acid Substances 0.000 description 23
238000002329 infrared spectrum Methods 0.000 description 22
239000000243 solution Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
239000003480 eluent Substances 0.000 description 18
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
229940086542 triethylamine Drugs 0.000 description 15
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 13
238000003756 stirring Methods 0.000 description 13
239000000126 substance Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
239000003826 tablet Substances 0.000 description 12
230000000875 corresponding effect Effects 0.000 description 11
239000004480 active ingredient Substances 0.000 description 10
238000000746 purification Methods 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
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 9
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 9
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
125000001931 aliphatic group Chemical group 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000012071 phase Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
VOKUMXABRRXHAR-UHFFFAOYSA-N 2-methyl-3-oxopropanoic acid Chemical compound O=CC(C)C(O)=O VOKUMXABRRXHAR-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
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235000013855 polyvinylpyrrolidone Nutrition 0.000 description 7
DWCNNQOORRREID-UHFFFAOYSA-N 1,2-dichloroethane;methanol Chemical compound OC.ClCCCl DWCNNQOORRREID-UHFFFAOYSA-N 0.000 description 6
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235000019359 magnesium stearate Nutrition 0.000 description 6
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150000003254 radicals Chemical class 0.000 description 6
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229920001223 polyethylene glycol Polymers 0.000 description 3
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238000007127 saponification reaction Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000012216 screening Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 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
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000001993 wax Substances 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
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD87304898A 1986-07-16 1987-07-13 Verfahren zur herstellung neuer benzolsulfonamide-indanylverbindungen DD264425A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3623944A DE3623944A1 (de)	1986-07-16	1986-07-16	Neue benzolsulfonamido-indanylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
DD264425A5 true DD264425A5 (de)	1989-02-01

Family

ID=6305263

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87304898A DD264425A5 (de)	1986-07-16	1987-07-13	Verfahren zur herstellung neuer benzolsulfonamide-indanylverbindungen

Country Status (15)

Country	Link
US (2)	US4820705A (da)
EP (1)	EP0253321A3 (da)
JP (1)	JPS6323853A (da)
AU (1)	AU604030B2 (da)
DD (1)	DD264425A5 (da)
DE (1)	DE3623944A1 (da)
DK (1)	DK362787A (da)
FI (1)	FI873142A7 (da)
HU (1)	HU196362B (da)
IL (1)	IL83198A (da)
NO (1)	NO165237C (da)
NZ (1)	NZ221081A (da)
PH (1)	PH24712A (da)
PT (1)	PT85335B (da)
ZA (1)	ZA875166B (da)

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* Cited by examiner, † Cited by third party
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GB8609331D0 (en) *	1986-04-16	1986-05-21	Pfizer Ltd	Anti-arrythmia agents
US5190975A (en) *	1987-11-18	1993-03-02	Tanabe Seiyaku Co., Ltd.	Indan derivatives used for treating thromboses or asthma
IL88314A (en) *	1987-11-18	1994-05-30	Tanabe Seiyaku Co	Sulphonylamino indane derivatives, their preparation and pharmaceutical compositions containing them
JPH02231464A (ja) *	1988-02-26	1990-09-13	Tanabe Seiyaku Co Ltd	インダンオキシ酢酸誘導体
DE3829455A1 (de) *	1988-08-31	1990-03-15	Boehringer Mannheim Gmbh	Sulfonamidoalkyl-cyclohexan-verbindungen, verfahren zu ihrer herstellung sowie arzneimittel
JPH02169563A (ja) *	1988-12-22	1990-06-29	Tanabe Seiyaku Co Ltd	インダン誘導体の製法及びその合成中間体
JPH0662547B2 (ja) *	1989-01-10	1994-08-17	田辺製薬株式会社	グリシン誘導体
FR2645537B1 (fr) *	1989-04-05	1994-03-04	Fabre Medicament Pierre	Nouveaux sulfonamides derives d'acides benzocycliques ou benzoheterocycliques, leur preparation et leur application en therapeutique
JPH0784381B2 (ja) *	1989-05-11	1995-09-13	田辺製薬株式会社	トロンボキサンａ▲下２▼拮抗薬
DE3932403A1 (de) *	1989-05-12	1991-04-11	Thomae Gmbh Dr K	Neue arylsulfonamide, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
JPH0372419A (ja) *	1989-05-16	1991-03-27	Tanabe Seiyaku Co Ltd	トロンボキサンａ↓２拮抗剤
JPH02149553A (ja) *	1989-09-28	1990-06-08	Tanabe Seiyaku Co Ltd	インダン誘導体及びその製法
US5206428A (en) *	1989-11-16	1993-04-27	Tanabe Seiyaku Co., Ltd.	Tetrahydronaphthalene derivatives and preparation thereof
US5206418A (en) *	1989-11-16	1993-04-27	Tanabe Seiyaku Co., Ltd.	Amino-tetrahydronaphthalene derivatives
DK0589037T3 (da) *	1991-03-01	1996-09-16	Zeria Pharm Co Ltd	Indanderivat og thromboxanantagonist indeholdende samme
JPH07106387B2 (ja) *	1991-06-25	1995-11-15	互栄機械株式会社	長尺な管棒材のロール矯正装置
CA2099743A1 (en) *	1992-07-02	1994-01-03	Akihiko Ishida	Pyridazinone derivatives and processes for preparing the same
US5739132A (en) *	1992-07-02	1998-04-14	Tanabe Seiyaku Co., Ltd.	Pyridazinone derivatives and processes for preparing the same
GB9220137D0 (en) *	1992-09-23	1992-11-04	Pfizer Ltd	Therapeutic agents
JP2506604B2 (ja) *	1993-04-07	1996-06-12	株式会社西山製作所	延性を向上した冷間引抜鋼管の製造方法
CA2139088A1 (en) *	1993-12-28	1995-06-29	Akihiko Ishida	Indane derivatives, processes for preparing the same and synthetic intermediate of the same
CA2138812A1 (en) *	1993-12-28	1995-06-29	Akihiko Ishida	Indane derivative and processes for preparing the same
IL118631A (en) *	1995-06-27	2002-05-23	Tanabe Seiyaku Co	History of pyridazinone and processes for their preparation
DE19749453A1 (de) *	1997-11-10	1999-05-12	Hoechst Marion Roussel De Gmbh	Sulfonamid-substituierte anellierte 5-Ring-Verbindungen, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen
WO2000005234A1 (en) *	1998-07-22	2000-02-03	Suntory Limited	NF-λB INHIBITORS CONTAINING INDAN DERIVATIVES AS THE ACTIVE INGREDIENT
US6933410B2 (en) *	2002-03-08	2005-08-23	Novartis Ag	Process for preparing 5,6-diethyl-2,3-dihydro-1H-inden-2-amine
WO2008061006A1 (en) *	2006-11-10	2008-05-22	Wyeth	Substituted indan-2-yl, tetrahydronaphthalen-2-yl, or dihydr0-2h-chr0men-3-yl arylsulfonamides and methods of their use
EP2011786A1 (en) *	2007-07-05	2009-01-07	Laboratorios del Dr. Esteve S.A.	Indane-amine derivatives, their preparation and use as medicaments
CN106431998B (zh) *	2016-09-27	2017-12-19	中国林业科学研究院林产化学工业研究所	N‑[4‑(异海松酰胺基)苯基]芳磺酰胺类化合物及其制备方法与抗癌活性应用
KR20200132858A (ko)	2018-03-20	2020-11-25	에자이 알앤드디 매니지먼트 가부시키가이샤	간질 치료제
US20240190809A1 (en) *	2021-05-11	2024-06-13	Awakn Ls Europe Holdings Limited	Therapeutic aminoindane compounds and compositions

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Publication number	Priority date	Publication date	Assignee	Title
US3383414A (en) *	1964-08-26	1968-05-14	Sandoz Ag	Benzocycloalkyl sulfamides
ES8101067A1 (es) *	1978-08-25	1980-12-01	Thomae Gmbh Dr K	Procedimiento para la preparacion de nuevos bencimidazoles sustituidos en posicion 5 o 6 con un anillo de piridazinona
US4233457A (en) *	1979-05-17	1980-11-11	Merck & Co., Inc.	Process for preparing indenyl acetic acids
EP0194548A3 (de) *	1985-03-12	1988-08-17	Dr. Karl Thomae GmbH	Neue Sulfonylaminoäthylverbindungen, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
IT1190371B (it) *	1985-06-19	1988-02-16	Zambon Spa	Processo per la preparazione dell'acido cis-5-fluoro-2-metil-1-(4-metiltiobenziliden)-indenil-3-acetico

1986
- 1986-07-16 DE DE3623944A patent/DE3623944A1/de not_active Withdrawn
1987
- 1987-07-10 EP EP87109962A patent/EP0253321A3/de not_active Withdrawn
- 1987-07-13 DD DD87304898A patent/DD264425A5/de not_active IP Right Cessation
- 1987-07-13 DK DK362787A patent/DK362787A/da not_active Application Discontinuation
- 1987-07-15 PT PT85335A patent/PT85335B/pt not_active IP Right Cessation
- 1987-07-15 JP JP62175022A patent/JPS6323853A/ja active Pending
- 1987-07-15 ZA ZA875166A patent/ZA875166B/xx unknown
- 1987-07-15 HU HU873240A patent/HU196362B/hu unknown
- 1987-07-15 NO NO872946A patent/NO165237C/no unknown
- 1987-07-15 IL IL83198A patent/IL83198A/xx unknown
- 1987-07-15 PH PH35548A patent/PH24712A/en unknown
- 1987-07-15 NZ NZ221081A patent/NZ221081A/en unknown
- 1987-07-16 AU AU75733/87A patent/AU604030B2/en not_active Ceased
- 1987-07-16 FI FI873142A patent/FI873142A7/fi not_active Application Discontinuation
- 1987-07-16 US US07/073,950 patent/US4820705A/en not_active Expired - Fee Related
1989
- 1989-02-01 US US07/305,255 patent/US4929754A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU604030B2 (en)	1990-12-06
PT85335B (pt)	1990-04-30
US4820705A (en)	1989-04-11
FI873142A0 (fi)	1987-07-16
EP0253321A2 (de)	1988-01-20
NO872946L (no)	1988-01-18
DK362787A (da)	1988-01-17
HUT44489A (en)	1988-03-28
NO165237C (no)	1991-01-16
PH24712A (en)	1990-10-01
NO872946D0 (no)	1987-07-15
FI873142A7 (fi)	1988-01-17
DK362787D0 (da)	1987-07-13
IL83198A (en)	1991-08-16
JPS6323853A (ja)	1988-02-01
PT85335A (de)	1987-08-01
HU196362B (en)	1988-11-28
US4929754A (en)	1990-05-29
EP0253321A3 (de)	1989-03-29
ZA875166B (en)	1989-03-29
IL83198A0 (en)	1987-12-31
AU7573387A (en)	1988-01-21
NZ221081A (en)	1990-04-26
DE3623944A1 (de)	1988-02-11
NO165237B (no)	1990-10-08

Legal Events

Date	Code	Title	Description
2001-02-15	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD264425A5 (de)	1989-02-01	Verfahren zur herstellung neuer benzolsulfonamide-indanylverbindungen
EP0194548A2 (de)	1986-09-17	Neue Sulfonylaminoäthylverbindungen, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
FR2690919A1 (fr)	1993-11-12	Dérivés de l'indole.
DE69705324T2 (de)	2001-10-11	N-hydroxyharnstoffderivate und sie enthaltende medizinische zubereitungen
AT395589B (de)	1993-01-25	Antihypercholesterinaemische tetrazol-verbindungen
EP0171702A1 (en)	1986-02-19	Benzoxazinone derivatives, preparation and use
DD149071A5 (de)	1981-06-24	Herstellung 2-substituierter trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole
DE3312675A1 (de)	1983-10-13	Phenoxyalkylcarbonsaeurederivate
DD209446A5 (de)	1984-05-09	Verfahren zur herstellung von neuen aromatischen verbindungen
EP0008645B1 (de)	1984-09-05	Alkoxyphenylpyrrolidone, Verfahren zu ihrer Herstellung und Arzneimittel auf Basis dieser Verbindungen
US4933354A (en)	1990-06-12	2-pyrrolidone-5-carboxylic acid compounds useful for the treatment of mental disorders
DE3721260A1 (de)	1989-01-12	Neue indolylpropanole, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen
EP0262395A2 (de)	1988-04-06	Sulfonamido-äthylverbindungen, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
EP0078241A2 (de)	1983-05-04	Furane
EP0059688A1 (de)	1982-09-08	Pyridazinone, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen und deren Verwendung
DE69526413T2 (de)	2002-10-31	Heterocyclische Carboxyalkylderivate
DE60207273T2 (de)	2006-07-20	Aminopyrrolverbindungen als entzündungshemmende Wirkstoffe
DE3132915A1 (de)	1983-03-03	1,5-diphenylpyrazolin-3-on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0172141B1 (de)	1988-12-07	Substituierte Pyridazinone, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen und deren Verwendung
DE3016304C2 (da)	1989-02-02
EP0389425A1 (de)	1990-09-26	Neue Benzothiopyranylamine
DE3534765A1 (de)	1987-04-02	Acylanilide enthaltende arzneimittel, neue acylanilide, deren verwendung und verfahren zu ihrer herstellung
HU197310B (en)	1989-03-28	Process for producing new quinaldinamide derivatives
EP0663395B1 (de)	2001-05-16	3-(Phenylalkylaminoalkyloxy)-5-phenylpyrazol-Derivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als herzfrequenzsenkendes Mittel
EP0082109A2 (de)	1983-06-22	Substituierte 2-Hydroxy-phenylessigsäuren und Derivate davon