DE2243202C2 - Verfahren zur Herstellung von 4-Chlormethyl- und 4-Brommethylcumarinen - Google Patents
Verfahren zur Herstellung von 4-Chlormethyl- und 4-BrommethylcumarinenInfo
- Publication number
- DE2243202C2 DE2243202C2 DE2243202A DE2243202A DE2243202C2 DE 2243202 C2 DE2243202 C2 DE 2243202C2 DE 2243202 A DE2243202 A DE 2243202A DE 2243202 A DE2243202 A DE 2243202A DE 2243202 C2 DE2243202 C2 DE 2243202C2
- Authority
- DE
- Germany
- Prior art keywords
- chloromethyl
- methyl
- coumarin
- sulfuric acid
- chloroform
- 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
- 238000000034 method Methods 0.000 title claims description 10
- JFDNDAIFYLKIBV-UHFFFAOYSA-N 4-(bromomethyl)chromen-2-one Chemical class C1=CC=CC2=C1OC(=O)C=C2CBr JFDNDAIFYLKIBV-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- -1 phenyl ester Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 235000001671 coumarin Nutrition 0.000 description 6
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- TXSLBPGPBNGHRW-UHFFFAOYSA-N 4-(chloromethyl)-7-hydroxychromen-2-one Chemical compound ClCC1=CC(=O)OC2=CC(O)=CC=C21 TXSLBPGPBNGHRW-UHFFFAOYSA-N 0.000 description 5
- DOPIYKOJONGIEE-UHFFFAOYSA-N 4-(chloromethyl)chromen-2-one Chemical compound C1=CC=CC2=C1OC(=O)C=C2CCl DOPIYKOJONGIEE-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229960000956 coumarin Drugs 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BPTQBPCEIVJHSK-UHFFFAOYSA-N 4-(bromomethyl)-5,7-dimethylchromen-2-one Chemical compound BrCC1=CC(=O)OC2=CC(C)=CC(C)=C21 BPTQBPCEIVJHSK-UHFFFAOYSA-N 0.000 description 3
- RLYROAVJCHAFFW-UHFFFAOYSA-N 4-(bromomethyl)-7-methylchromen-2-one Chemical compound BrCC1=CC(=O)OC2=CC(C)=CC=C21 RLYROAVJCHAFFW-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- FFFLTPZFXWCHCT-UHFFFAOYSA-N 4-(chloromethyl)-7-methylchromen-2-one Chemical compound ClCC1=CC(=O)OC2=CC(C)=CC=C21 FFFLTPZFXWCHCT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- VIIIJFZJKFXOGG-UHFFFAOYSA-N 3-methylchromen-2-one Chemical compound C1=CC=C2OC(=O)C(C)=CC2=C1 VIIIJFZJKFXOGG-UHFFFAOYSA-N 0.000 description 1
- ZKVDUCAPTIXCSV-UHFFFAOYSA-N 4-(chloromethyl)-5,7,8-trimethylchromen-2-one Chemical compound ClCC1=CC(=O)OC2=C(C)C(C)=CC(C)=C21 ZKVDUCAPTIXCSV-UHFFFAOYSA-N 0.000 description 1
- UCTNTYHJFWMUBD-UHFFFAOYSA-N 4-chloro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CCl UCTNTYHJFWMUBD-UHFFFAOYSA-N 0.000 description 1
- WSHVQVCBPLNREW-UHFFFAOYSA-N 4-chloro-3-oxobutanoyl chloride Chemical compound ClCC(=O)CC(Cl)=O WSHVQVCBPLNREW-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- DSTPUJAJSXTJHM-UHFFFAOYSA-N isothymol Natural products CC(C)C1=CC(C)=CC=C1O DSTPUJAJSXTJHM-UHFFFAOYSA-N 0.000 description 1
- YOXFUEHEPATFOW-UHFFFAOYSA-N methanol;2-methylphenol Chemical compound OC.CC1=CC=CC=C1O YOXFUEHEPATFOW-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N para-hydroxytoluene Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
Classifications
-
- 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
- C07D311/18—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 otherwise than in position 3 or 7
-
- 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
-
- 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
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1293771A CH541553A (de) | 1971-09-03 | 1971-09-03 | Verfahren zur Herstellung von 4-Halogenmethylcumarinen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2243202A1 DE2243202A1 (de) | 1973-03-08 |
| DE2243202C2 true DE2243202C2 (de) | 1983-08-11 |
Family
ID=4387795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2243202A Expired DE2243202C2 (de) | 1971-09-03 | 1972-09-01 | Verfahren zur Herstellung von 4-Chlormethyl- und 4-Brommethylcumarinen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3808232A (enExample) |
| JP (1) | JPS5724350B2 (enExample) |
| AT (1) | AT315829B (enExample) |
| BE (1) | BE788200A (enExample) |
| CA (1) | CA995230A (enExample) |
| CH (1) | CH541553A (enExample) |
| DE (1) | DE2243202C2 (enExample) |
| FR (1) | FR2151082B1 (enExample) |
| GB (1) | GB1332768A (enExample) |
| IT (1) | IT1019013B (enExample) |
| LU (1) | LU65992A1 (enExample) |
| NL (1) | NL7206587A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3891569A (en) * | 1974-02-11 | 1975-06-24 | Us Navy | Lasing dyes |
| GB2168696B (en) * | 1984-12-21 | 1989-01-11 | Boehringer Biochemia Srl | Fluoro coumarins as antilymphoedema agents |
| US4650881A (en) * | 1985-04-01 | 1987-03-17 | Iowa State University Research Foundation, Inc. | Synthesis of isocoumarins via thallation-olefination of arenes |
| US4647666A (en) * | 1985-04-01 | 1987-03-03 | Iowa State University Research Foundation, Inc. | Heterocyclic synthesis via thallation and subsequent palladium-promoted olefination |
| US5356929A (en) * | 1989-01-23 | 1994-10-18 | Lehigh University | Reduced and quaternized psoralens as photo-activated therapeutics |
| DE69229174T2 (de) * | 1991-08-23 | 1999-09-16 | Molecular Probes, Inc. | Verwendung von haloalkylderivaten von reportermolekülen zur analyse der metabolischen aktivität in zellen |
| USRE38723E1 (en) * | 1991-08-23 | 2005-04-12 | Molecular Probes, Inc. | Haloalkyl derivatives of reporter molecules used to analyze metabolic activity in cells |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB834903A (en) * | 1955-09-28 | 1960-05-11 | Bayer Ag | Method of optically brightening materials |
-
0
- BE BE788200D patent/BE788200A/xx unknown
-
1971
- 1971-09-03 CH CH1293771A patent/CH541553A/de not_active IP Right Cessation
-
1972
- 1972-05-08 GB GB2137772A patent/GB1332768A/en not_active Expired
- 1972-05-16 NL NL7206587A patent/NL7206587A/xx not_active Application Discontinuation
- 1972-06-20 IT IT51008/72A patent/IT1019013B/it active
- 1972-07-21 JP JP7331572A patent/JPS5724350B2/ja not_active Expired
- 1972-07-28 US US00275956A patent/US3808232A/en not_active Expired - Lifetime
- 1972-08-28 CA CA150,360A patent/CA995230A/en not_active Expired
- 1972-09-01 AT AT752772A patent/AT315829B/de not_active IP Right Cessation
- 1972-09-01 FR FR7231099A patent/FR2151082B1/fr not_active Expired
- 1972-09-01 LU LU65992A patent/LU65992A1/xx unknown
- 1972-09-01 DE DE2243202A patent/DE2243202C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7206587A (enExample) | 1973-03-06 |
| IT1019013B (it) | 1977-11-10 |
| US3808232A (en) | 1974-04-30 |
| FR2151082B1 (enExample) | 1978-02-10 |
| DE2243202A1 (de) | 1973-03-08 |
| GB1332768A (en) | 1973-10-03 |
| CA995230A (en) | 1976-08-17 |
| BE788200A (fr) | 1973-02-28 |
| AT315829B (de) | 1974-06-10 |
| CH541553A (de) | 1973-09-15 |
| FR2151082A1 (enExample) | 1973-04-13 |
| LU65992A1 (enExample) | 1973-03-12 |
| JPS5724350B2 (enExample) | 1982-05-24 |
| JPS4834168A (enExample) | 1973-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8181 | Inventor (new situation) |
Free format text: HARDT, PETER, DIPL.-CHEM. DR., NEUENBURG, CH BOOSEN, KARL-JOSEF, DIPL.-CHEM. DR., ERLACH, CH |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |