DE2724682C2 - Chromeno[4,3-b]indolverbindungen - Google Patents
Chromeno[4,3-b]indolverbindungenInfo
- Publication number
- DE2724682C2 DE2724682C2 DE2724682A DE2724682A DE2724682C2 DE 2724682 C2 DE2724682 C2 DE 2724682C2 DE 2724682 A DE2724682 A DE 2724682A DE 2724682 A DE2724682 A DE 2724682A DE 2724682 C2 DE2724682 C2 DE 2724682C2
- Authority
- DE
- Germany
- Prior art keywords
- benzyl
- phenyl
- formula
- halogen
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KRLBKAYYJSNNKC-UHFFFAOYSA-N chromeno[4,3-b]indole Chemical class C1=CC=C2C3=NC4=CC=CC=C4C3=COC2=C1 KRLBKAYYJSNNKC-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- -1 pyrrolidino, piperidino Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229930194542 Keto Natural products 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000002253 acid Substances 0.000 description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
- 239000004927 clay Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- WKZRPPBUMLPCRF-UHFFFAOYSA-N 2-(1h-indol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC2=CC=CC=C2N1 WKZRPPBUMLPCRF-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- FMDCKUQJSQBMBZ-UHFFFAOYSA-N 4-chloro-2-(1h-indol-2-yl)phenol Chemical compound OC1=CC=C(Cl)C=C1C1=CC2=CC=CC=C2N1 FMDCKUQJSQBMBZ-UHFFFAOYSA-N 0.000 description 1
- BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Photoreceptors In Electrophotography (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH711576A CH618639A5 (en, 2012) | 1976-06-04 | 1976-06-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2724682A1 DE2724682A1 (de) | 1977-12-15 |
| DE2724682C2 true DE2724682C2 (de) | 1986-09-18 |
Family
ID=4320194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2724682A Expired DE2724682C2 (de) | 1976-06-04 | 1977-06-01 | Chromeno[4,3-b]indolverbindungen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4123439A (en, 2012) |
| JP (1) | JPS6011039B2 (en, 2012) |
| AR (1) | AR217075A1 (en, 2012) |
| AT (1) | AT352153B (en, 2012) |
| BE (1) | BE855360A (en, 2012) |
| BR (1) | BR7703615A (en, 2012) |
| CA (1) | CA1083576A (en, 2012) |
| CH (1) | CH618639A5 (en, 2012) |
| DE (1) | DE2724682C2 (en, 2012) |
| FR (1) | FR2353554A1 (en, 2012) |
| GB (1) | GB1550328A (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023991B2 (ja) * | 1976-08-24 | 1985-06-10 | 富士写真フイルム株式会社 | インドロクロメンを使つた記録材料 |
| EP0001248B1 (de) * | 1977-09-19 | 1980-10-01 | Ciba-Geigy Ag | Benzopyranothiazole, ihre Herstellung und ihre Verwendung in druck- oder wärmeempfindlichem Aufzeichnungsmaterial |
| JPS6313778A (ja) * | 1986-07-04 | 1988-01-21 | Fuji Photo Film Co Ltd | 記録材料 |
| JPS6317077A (ja) * | 1986-07-09 | 1988-01-25 | Fuji Photo Film Co Ltd | 記録材料 |
| JPS6317078A (ja) * | 1986-07-09 | 1988-01-25 | Fuji Photo Film Co Ltd | 記録材料 |
| JPS6362778A (ja) * | 1986-09-03 | 1988-03-19 | Fuji Photo Film Co Ltd | 記録材料 |
| JPS6367179A (ja) * | 1986-09-08 | 1988-03-25 | Fuji Photo Film Co Ltd | 記録シ−ト |
| JPS6367180A (ja) * | 1986-09-09 | 1988-03-25 | Fuji Photo Film Co Ltd | 記録シ−ト |
| JPS63158287A (ja) * | 1986-12-22 | 1988-07-01 | Fuji Photo Film Co Ltd | 記録材料 |
| US6001866A (en) * | 1995-10-05 | 1999-12-14 | Warner-Lambert Company | Method for treating and preventing inflammation and atherosclerosis |
| PL349192A1 (en) * | 1998-12-18 | 2002-07-01 | Axys Pharmaceuticals | Protease inhibitors |
-
1976
- 1976-06-04 CH CH711576A patent/CH618639A5/de not_active IP Right Cessation
-
1977
- 1977-05-20 US US05/799,063 patent/US4123439A/en not_active Expired - Lifetime
- 1977-06-01 DE DE2724682A patent/DE2724682C2/de not_active Expired
- 1977-06-02 GB GB23488/77A patent/GB1550328A/en not_active Expired
- 1977-06-02 AR AR267921A patent/AR217075A1/es active
- 1977-06-02 CA CA279,735A patent/CA1083576A/en not_active Expired
- 1977-06-03 BR BR7703615A patent/BR7703615A/pt unknown
- 1977-06-03 AT AT396177A patent/AT352153B/de not_active IP Right Cessation
- 1977-06-03 BE BE178166A patent/BE855360A/xx not_active IP Right Cessation
- 1977-06-03 JP JP52064923A patent/JPS6011039B2/ja not_active Expired
- 1977-06-03 FR FR7716953A patent/FR2353554A1/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6011039B2 (ja) | 1985-03-22 |
| AR217075A1 (es) | 1980-02-29 |
| FR2353554B1 (en, 2012) | 1980-02-15 |
| DE2724682A1 (de) | 1977-12-15 |
| GB1550328A (en) | 1979-08-08 |
| BE855360A (fr) | 1977-12-05 |
| CA1083576A (en) | 1980-08-12 |
| CH618639A5 (en, 2012) | 1980-08-15 |
| AT352153B (de) | 1979-09-10 |
| ATA396177A (de) | 1979-02-15 |
| US4123439A (en) | 1978-10-31 |
| JPS52148099A (en) | 1977-12-08 |
| FR2353554A1 (fr) | 1977-12-30 |
| BR7703615A (pt) | 1978-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2323803C3 (de) | Spirodipyrane und deren Verwendung als Farbbildner für Kopierverfahren | |
| DE2724682C2 (de) | Chromeno[4,3-b]indolverbindungen | |
| DE1768862B2 (de) | Basisch substituierte fluorane, verfahren zu ihrer herstellung und deren verwendung als farbbildner fuer kopiermaterialien | |
| DE2842263C2 (en, 2012) | ||
| EP0138177A2 (de) | Fluorane und deren Verwendung | |
| DE3116815A1 (de) | Chromogenes material | |
| DE2703008A1 (de) | Indolinospiropyranverbindungen | |
| DE1795344B2 (de) | Verfahren zur herstellung von 3-aminoisothiazolen | |
| DE3905339A1 (de) | Chinolin-4-carbonsaeurederivate und deren verwendung | |
| DE2004873B2 (de) | Neue Borderivate, deren Herstellung und Zusammensetzungen, die diese enthalten | |
| DE2627223A1 (de) | Verfahren zur herstellung von 4-benzoylpyrazol-derivaten | |
| DE2451897A1 (de) | 3-diaethylamino-2,2-dimethylpropyl 5-(substituierte phenyl)-2-furoate | |
| DE1695092C3 (de) | N-(4-Sulfonamidophenyl)-a-alkylsuccin!mideund deren Salze mit Basen, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen | |
| DE1645978B2 (de) | 5-Nitro-2-furyl-chinolin-derivate und Verfahren zu ihrer Herstellung | |
| DE1011887B (de) | Verfahren zur Herstellung von in 10-Stellung basisch substituierten Phenthiazinabkoemmlingen | |
| DE2240991C2 (de) | Basisch substituierte Fluoranverbindungen und ihre Verwendung | |
| DE875048C (de) | Verfahren zur Herstellung von 3-Pyrazolidonen | |
| DE1220434B (de) | Verfahren zur Herstellung von am kernstaendigen Stickstoffatom substituierten 2-Sulfamyl-4-trifluormethylanilin-Verbindungen | |
| DE2644789A1 (de) | Alkylen-di-phenylalk(en)ylcarbonsaeuren und ihre herstellung und verwendung | |
| DE1242603B (de) | Verfahren zur Herstellung von 5-Hydroxy-5-aminoalkyl-di-benzo-[a, d]-cycloheptanen | |
| DE2515306A1 (de) | Pyrazoloxanthen-verbindungen, verfahren zu ihrer herstellung und ihre verwendung | |
| DE1247316B (de) | Verfahren zur Herstellung einer farbbildenden, monomeren Verbindung fuer die Farbphotographie | |
| DE870270C (de) | Verfahren zur Herstellung von Xantheniumverbindungen | |
| AT276436B (de) | Verfahren zur Herstellung von neuen Sulfonylharnstoffderivaten | |
| AT383544B (de) | Verwendung chromogener indolizinylgruppen aufweisender lactone in druck- oder waermeempfindlichem aufzeichungsmaterial |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: REDIES, B., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 40 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |