DE2528698C3 - 7-Sulfonylacetylamino-substituierte Cumarinverbindungen und ein Verfahren zu deren Herstellung sowie die Verwendung dieser Verbindungen zur Herstellung von optischer Cumarin-Aufhellern - Google Patents
7-Sulfonylacetylamino-substituierte Cumarinverbindungen und ein Verfahren zu deren Herstellung sowie die Verwendung dieser Verbindungen zur Herstellung von optischer Cumarin-AufhellernInfo
- Publication number
- DE2528698C3 DE2528698C3 DE2528698A DE2528698A DE2528698C3 DE 2528698 C3 DE2528698 C3 DE 2528698C3 DE 2528698 A DE2528698 A DE 2528698A DE 2528698 A DE2528698 A DE 2528698A DE 2528698 C3 DE2528698 C3 DE 2528698C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- coumarin
- production
- brighteners
- sulfonylacetylamino
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title description 16
- 229960000956 coumarin Drugs 0.000 title description 11
- 235000001671 coumarin Nutrition 0.000 title description 8
- 230000003287 optical effect Effects 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000004775 coumarins Chemical class 0.000 title description 3
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940018563 3-aminophenol Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- MTSUMMNWZVEZBD-UHFFFAOYSA-N 1,3,5-trimethyl-1,3,5-triazinan-3-ium-2,4-dione;bromide Chemical compound [Br-].CN1C[NH+](C)C(=O)N(C)C1=O MTSUMMNWZVEZBD-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 2
- -1 4-chloropyrazolyl Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229960004909 aminosalicylic acid Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- SFMIGFOCOPOAFP-UHFFFAOYSA-N n-(4-formyl-3-hydroxyphenyl)benzenesulfonamide Chemical compound C1=C(C=O)C(O)=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 SFMIGFOCOPOAFP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- UOLKUOBCZVAOEZ-UHFFFAOYSA-N 1,3-dimethyl-1-(methylcarbamoyl)urea Chemical compound CNC(=O)N(C)C(=O)NC UOLKUOBCZVAOEZ-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- JUHWNNRXPDCINW-UHFFFAOYSA-N 3-chloro-n-(4-formyl-3-hydroxyphenyl)benzenesulfonamide Chemical compound C1=C(C=O)C(O)=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 JUHWNNRXPDCINW-UHFFFAOYSA-N 0.000 description 1
- KFCDSHMWJNXPAI-UHFFFAOYSA-N 4-amino-2-methoxybenzaldehyde Chemical compound COC1=CC(N)=CC=C1C=O KFCDSHMWJNXPAI-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QMVODOBDWWGARP-UHFFFAOYSA-N N-(4-formyl-3-hydroxyphenyl)-1-phenylmethanesulfonamide Chemical compound C1=C(C=O)C(O)=CC(NS(=O)(=O)CC=2C=CC=CC=2)=C1 QMVODOBDWWGARP-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- MUSAAWZZZULDOS-UHFFFAOYSA-N OC(C=C(C=C1)NS(C2=CC=CC=C2)(=O)=O)=C1C1=NC=NC=N1 Chemical class OC(C=C(C=C1)NS(C2=CC=CC=C2)(=O)=O)=C1C1=NC=NC=N1 MUSAAWZZZULDOS-UHFFFAOYSA-N 0.000 description 1
- 101000831256 Oryza sativa subsp. japonica Cysteine proteinase inhibitor 1 Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VMMZXFBPVSLUAT-UHFFFAOYSA-N n-(4-formyl-3-hydroxyphenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C=O)C(O)=C1 VMMZXFBPVSLUAT-UHFFFAOYSA-N 0.000 description 1
- BHDPWJGTBSEZIM-UHFFFAOYSA-N n-(4-formyl-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C=O)C(O)=C1 BHDPWJGTBSEZIM-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/10—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2528698A DE2528698C3 (de) | 1975-06-27 | 1975-06-27 | 7-Sulfonylacetylamino-substituierte Cumarinverbindungen und ein Verfahren zu deren Herstellung sowie die Verwendung dieser Verbindungen zur Herstellung von optischer Cumarin-Aufhellern |
| US05/698,925 US4069228A (en) | 1975-06-27 | 1976-06-23 | Coumarins containing sulphonylamino groups |
| GB26288/76A GB1494460A (en) | 1975-06-27 | 1976-06-24 | Coumarins containing sulphonylamino groups |
| JP51074584A JPS525842A (en) | 1975-06-27 | 1976-06-25 | Coumarin having sulfonylamino group and process for manufacture thereof |
| BE168296A BE843394A (enExample) | 1975-06-27 | 1976-06-25 | |
| FR7619328A FR2317299A1 (fr) | 1975-06-27 | 1976-06-25 | Coumarines contenant des groupes sulfonylamino, leur obtention et leur application a titre d'intermediaire pour la production de colorants et d'agents de blanchiment optique ou d'azurants |
| BR7604190A BR7604190A (pt) | 1975-06-27 | 1976-06-25 | Processo para a preparacao de cumarinas e sua aplicacao |
| IT24764/76A IT1061416B (it) | 1975-06-27 | 1976-06-25 | Cumarine contenenti gruppi solfonil..amminici |
| CH819176A CH605888A5 (enExample) | 1975-06-27 | 1976-06-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2528698A DE2528698C3 (de) | 1975-06-27 | 1975-06-27 | 7-Sulfonylacetylamino-substituierte Cumarinverbindungen und ein Verfahren zu deren Herstellung sowie die Verwendung dieser Verbindungen zur Herstellung von optischer Cumarin-Aufhellern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2528698A1 DE2528698A1 (de) | 1977-01-13 |
| DE2528698B2 DE2528698B2 (de) | 1981-02-05 |
| DE2528698C3 true DE2528698C3 (de) | 1982-03-18 |
Family
ID=5950082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2528698A Expired DE2528698C3 (de) | 1975-06-27 | 1975-06-27 | 7-Sulfonylacetylamino-substituierte Cumarinverbindungen und ein Verfahren zu deren Herstellung sowie die Verwendung dieser Verbindungen zur Herstellung von optischer Cumarin-Aufhellern |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4069228A (enExample) |
| JP (1) | JPS525842A (enExample) |
| BE (1) | BE843394A (enExample) |
| BR (1) | BR7604190A (enExample) |
| CH (1) | CH605888A5 (enExample) |
| DE (1) | DE2528698C3 (enExample) |
| FR (1) | FR2317299A1 (enExample) |
| GB (1) | GB1494460A (enExample) |
| IT (1) | IT1061416B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2902470A1 (de) * | 1979-01-23 | 1980-07-31 | Bayer Ag | Cumarin-verbindungen |
| US6766799B2 (en) * | 2001-04-16 | 2004-07-27 | Advanced Inhalation Research, Inc. | Inhalation device |
| US8496002B2 (en) * | 2007-06-12 | 2013-07-30 | Civitas Therapeutics, Inc. | Powder inhaler devices |
| CN118813133B (zh) * | 2024-09-14 | 2024-12-03 | 烟台大学 | 石墨烯型阻燃、耐光性、耐磨耗水性聚氨酯涂料的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL282249A (enExample) * | 1961-08-19 | |||
| US3156697A (en) * | 1962-11-29 | 1964-11-10 | Upjohn Co | Pyridylcoumarins |
| JPS4113944Y1 (enExample) * | 1964-03-03 | 1966-06-29 | ||
| DE1293160B (de) * | 1964-03-07 | 1969-04-24 | Bayer Ag | Verfahren zur Herstellung von Cumarinverbindungen |
| CH566359A5 (enExample) * | 1972-06-21 | 1975-09-15 | Ciba Geigy Ag |
-
1975
- 1975-06-27 DE DE2528698A patent/DE2528698C3/de not_active Expired
-
1976
- 1976-06-23 US US05/698,925 patent/US4069228A/en not_active Expired - Lifetime
- 1976-06-24 GB GB26288/76A patent/GB1494460A/en not_active Expired
- 1976-06-25 BE BE168296A patent/BE843394A/xx unknown
- 1976-06-25 JP JP51074584A patent/JPS525842A/ja active Granted
- 1976-06-25 BR BR7604190A patent/BR7604190A/pt unknown
- 1976-06-25 FR FR7619328A patent/FR2317299A1/fr active Granted
- 1976-06-25 CH CH819176A patent/CH605888A5/xx not_active IP Right Cessation
- 1976-06-25 IT IT24764/76A patent/IT1061416B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1494460A (en) | 1977-12-07 |
| BE843394A (enExample) | 1976-12-27 |
| IT1061416B (it) | 1983-02-28 |
| FR2317299B1 (enExample) | 1980-07-11 |
| DE2528698A1 (de) | 1977-01-13 |
| FR2317299A1 (fr) | 1977-02-04 |
| JPS525842A (en) | 1977-01-17 |
| US4069228A (en) | 1978-01-17 |
| BR7604190A (pt) | 1977-07-26 |
| CH605888A5 (enExample) | 1978-10-13 |
| DE2528698B2 (de) | 1981-02-05 |
| JPS5639786B2 (enExample) | 1981-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |