DE1795330A1 - Kondensierte Pyrrolverbindungen und Verfahren zu deren Herstellung - Google Patents
Kondensierte Pyrrolverbindungen und Verfahren zu deren HerstellungInfo
- Publication number
- DE1795330A1 DE1795330A1 DE19681795330 DE1795330A DE1795330A1 DE 1795330 A1 DE1795330 A1 DE 1795330A1 DE 19681795330 DE19681795330 DE 19681795330 DE 1795330 A DE1795330 A DE 1795330A DE 1795330 A1 DE1795330 A1 DE 1795330A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- aromatic
- water
- acid
- product
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 28
- 150000003233 pyrroles Chemical class 0.000 title description 6
- 239000000047 product Substances 0.000 claims description 52
- 239000002253 acid Substances 0.000 claims description 34
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- -1 alkpxy Chemical group 0.000 claims description 13
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 claims description 13
- 229960002327 chloral hydrate Drugs 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 150000004984 aromatic diamines Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 241000243251 Hydra Species 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims 1
- KRLLUZSLSSIQKH-UHFFFAOYSA-N pyrrolo[3,2-c]carbazole Chemical compound C12=CC=CC=C2N=C2C1=C1N=CC=C1C=C2 KRLLUZSLSSIQKH-UHFFFAOYSA-N 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000009835 boiling Methods 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 238000000921 elemental analysis Methods 0.000 description 18
- 238000002329 infrared spectrum Methods 0.000 description 18
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 150000002923 oximes Chemical class 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000012265 solid product Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- HYBVISCYJVVEDX-UHFFFAOYSA-N 4-(4-aminophenyl)-3-chloroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1Cl HYBVISCYJVVEDX-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical class C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 2
- NXZLTPQEYLXQCH-DAFODLJHSA-N (2e)-2-hydroxyiminoacetamide Chemical compound NC(=O)\C=N\O NXZLTPQEYLXQCH-DAFODLJHSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- FNJYNTJIZBHPGP-UHFFFAOYSA-N 2,5-dichlorobenzene-1,3-diamine Chemical compound NC1=CC(Cl)=CC(N)=C1Cl FNJYNTJIZBHPGP-UHFFFAOYSA-N 0.000 description 1
- KRACQCKFIKMTTP-UHFFFAOYSA-N 2,5-dimethylbenzene-1,3-diamine Chemical compound CC1=CC(N)=C(C)C(N)=C1 KRACQCKFIKMTTP-UHFFFAOYSA-N 0.000 description 1
- YCFUHBHONRJFHI-UHFFFAOYSA-N 2,6-dichloronaphthalene Chemical compound C1=C(Cl)C=CC2=CC(Cl)=CC=C21 YCFUHBHONRJFHI-UHFFFAOYSA-N 0.000 description 1
- ACYOAZKGYRXBII-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)-3-pyrrol-2-ylidenepyrrole Chemical class N1=CC=CC1=C1C(C=2NC=CC=2)=NC=C1 ACYOAZKGYRXBII-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 1
- ILPDVOFDSNNCNY-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(N)=C(C(O)=O)C=C1C(O)=O ILPDVOFDSNNCNY-UHFFFAOYSA-N 0.000 description 1
- ZDFDINMHFLFYGQ-UHFFFAOYSA-N 4-(4-aminophenyl)-2-methoxyaniline Chemical compound C1=C(N)C(OC)=CC(C=2C=CC(N)=CC=2)=C1 ZDFDINMHFLFYGQ-UHFFFAOYSA-N 0.000 description 1
- SZDCQDGTODDBKZ-UHFFFAOYSA-N 4-(4-aminophenyl)-2-methylaniline Chemical compound C1=C(N)C(C)=CC(C=2C=CC(N)=CC=2)=C1 SZDCQDGTODDBKZ-UHFFFAOYSA-N 0.000 description 1
- QHNJDSRKOHTZMY-UHFFFAOYSA-N 4-[(4-amino-3-bromophenyl)methyl]-2-bromoaniline Chemical compound C1=C(Br)C(N)=CC=C1CC1=CC=C(N)C(Br)=C1 QHNJDSRKOHTZMY-UHFFFAOYSA-N 0.000 description 1
- ZWPNSXUXJWRFIZ-UHFFFAOYSA-N 5-[(2,3-dioxo-1h-indol-5-yl)methyl]-1h-indole-2,3-dione Chemical class C1=C2NC(=O)C(=O)C2=CC(CC2=CC=C3NC(C(C3=C2)=O)=O)=C1 ZWPNSXUXJWRFIZ-UHFFFAOYSA-N 0.000 description 1
- CSWRPDRRIWFDDK-UHFFFAOYSA-N 5-[(2,3-dioxo-1h-indol-5-yl)oxy]-1h-indole-2,3-dione Chemical compound C1=C2NC(=O)C(=O)C2=CC(OC2=CC=C3NC(C(C3=C2)=O)=O)=C1 CSWRPDRRIWFDDK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PTFUNIMKNOPWPY-UHFFFAOYSA-N NC=1C(=C(C=C(C1)OC)N)Cl Chemical compound NC=1C(=C(C=C(C1)OC)N)Cl PTFUNIMKNOPWPY-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5833767 | 1967-09-13 | ||
| JP6653667A JPS4818225B1 (enExample) | 1967-10-18 | 1967-10-18 | |
| JP6803967 | 1967-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1795330A1 true DE1795330A1 (de) | 1970-04-16 |
Family
ID=27296561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681795330 Pending DE1795330A1 (de) | 1967-09-13 | 1968-09-13 | Kondensierte Pyrrolverbindungen und Verfahren zu deren Herstellung |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE720803A (enExample) |
| DE (1) | DE1795330A1 (enExample) |
| GB (1) | GB1251082A (enExample) |
| NL (1) | NL6813137A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0216165A1 (de) * | 1985-08-29 | 1987-04-01 | Roche Diagnostics GmbH | Neue Benzodipyrrole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150295179A1 (en) * | 2012-11-09 | 2015-10-15 | Yuning Li | Monomeric, oligomeric and polymeric semiconductors containing fused rings and their devices |
-
1968
- 1968-09-12 GB GB1251082D patent/GB1251082A/en not_active Expired
- 1968-09-13 NL NL6813137A patent/NL6813137A/xx unknown
- 1968-09-13 BE BE720803D patent/BE720803A/xx unknown
- 1968-09-13 DE DE19681795330 patent/DE1795330A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0216165A1 (de) * | 1985-08-29 | 1987-04-01 | Roche Diagnostics GmbH | Neue Benzodipyrrole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4874756A (en) * | 1985-08-29 | 1989-10-17 | Boehringer Mannheim Gmbh | Benzodipyrroles, processes for the preparation thereof and pharmaceutical compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1251082A (enExample) | 1971-10-27 |
| BE720803A (enExample) | 1969-02-17 |
| NL6813137A (enExample) | 1969-03-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1769423A1 (de) | Neue Disazoverbindungen,Verfahren zu deren Herstellung und Anwendung | |
| DE1225318B (de) | Verfahren zur Herstellung von Azofarbstoffen und deren Metallkomplexverbindungen | |
| DE1569712A1 (de) | Metallhaltige Azomethin-Pigmente | |
| DE1645174A1 (de) | Verfahren zur Herstellung von Polyimid | |
| DE1795330A1 (de) | Kondensierte Pyrrolverbindungen und Verfahren zu deren Herstellung | |
| DE2017764C3 (de) | Benzoxanthen- und Benzothioxanthenfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung. Anmi Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt | |
| DE1644287C (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| DE2841243C2 (de) | Kupplungskomponente, Verfahren zu deren Herstellung und deren Verwendung | |
| DE2505188C2 (de) | Von 4,4'-Diaminobenzanilid abgeleiteter wasserlöslicher Azo-farbstoff | |
| DE2533723A1 (de) | Monoazofarbstoffe | |
| DE19911267A1 (de) | Azoxyfarbstoffe und deren Cu-Komplexe | |
| DE1218635B (de) | Verfahren zur Herstellung von wasserunloeslichen, Arylhydrazonreste enthaltenden Azofarbstoffen | |
| DE1804461B2 (de) | Verfahren zur herstellung von copolymeren und deren verwendung | |
| DE46438C (de) | Verfahren zur Darstellung von Tetrazofarbstoffen aus Carbazo) | |
| DE1569710C (de) | Disazomethin Pigmente , Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE946170C (de) | Verfahren zur Herstellung kobalthaltiger Azofarbstoffe der Acylacetylaminoalkanreihe | |
| DE748914C (de) | Verfahren zur Herstellung von metallhaltigen Stilbenazofarbstoffen | |
| DE888734C (de) | Verfahren zur Herstellung der Kupferkomplexverbindungen von Trisazofarbstoffen | |
| DE1644257C3 (de) | Kupfer- oder Nickelkomplexe von Blsformazanfarbstoffen | |
| DE1544410C (de) | Verfahren zur Herstellung basischer Farbstoffe | |
| DE919169C (de) | Verfahren zur Herstellung von Kondensationsprodukten | |
| DE647015C (de) | Verfahren zur Herstellung von Kuepenfarbstoffen der Anthrachinonreihe | |
| DE633084C (de) | Verfahren zur Herstellung von Azoverbindungen | |
| AT226855B (de) | Verfahren zur Herstellung neuer basischer Hydrazonfarbstoffe | |
| DE1470173A1 (de) | Verfahren zur Herstellung von 1-{3-{[5,6,7,8-Tetra-hydro-4-(arylazo)-1-naphthyl]amino}propyl}-piperidinverbindungen |