DE2204051A1 - 3 (Hydroxymethyl)-chromone und Verfahren zu ihrer Herstellung - Google Patents
3 (Hydroxymethyl)-chromone und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2204051A1 DE2204051A1 DE19722204051 DE2204051A DE2204051A1 DE 2204051 A1 DE2204051 A1 DE 2204051A1 DE 19722204051 DE19722204051 DE 19722204051 DE 2204051 A DE2204051 A DE 2204051A DE 2204051 A1 DE2204051 A1 DE 2204051A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxymethyl
- chromone
- methylsulfinyl
- chromanone
- chloro
- 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 6
- 238000002360 preparation method Methods 0.000 title description 4
- KNBXEQXDBQSZBV-UHFFFAOYSA-N 2-(hydroxymethyl)chromen-4-one Chemical class C1=CC=C2OC(CO)=CC(=O)C2=C1 KNBXEQXDBQSZBV-UHFFFAOYSA-N 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 33
- -1 7-acetamido-3- (hydroxymethyl) chromone Chemical compound 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- CCUIZOSFSPCGLS-UHFFFAOYSA-N 3-(hydroxymethyl)chromen-4-one Chemical compound C1=CC=C2C(=O)C(CO)=COC2=C1 CCUIZOSFSPCGLS-UHFFFAOYSA-N 0.000 claims description 5
- KPDOKBVZTGPKEH-UHFFFAOYSA-N 6-chloro-3-(hydroxymethyl)chromen-4-one Chemical compound C1=C(Cl)C=C2C(=O)C(CO)=COC2=C1 KPDOKBVZTGPKEH-UHFFFAOYSA-N 0.000 claims description 4
- JNASZVCFXUQYET-UHFFFAOYSA-N 3-(hydroxymethyl)-3-methylsulfinyl-2h-chromen-4-one Chemical compound C1=CC=C2C(=O)C(S(=O)C)(CO)COC2=C1 JNASZVCFXUQYET-UHFFFAOYSA-N 0.000 claims description 3
- KQAZERJEHBYXGV-UHFFFAOYSA-N 6-hydroxy-3-(hydroxymethyl)-3-methylsulfinyl-2H-chromen-4-one Chemical compound OC=1C=C2C(C(COC2=CC1)(S(=O)C)CO)=O KQAZERJEHBYXGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- XHZNEGARHSRQKO-UHFFFAOYSA-N 3-(hydroxymethyl)-5-methoxychromen-4-one Chemical compound O1C=C(CO)C(=O)C2=C1C=CC=C2OC XHZNEGARHSRQKO-UHFFFAOYSA-N 0.000 claims description 2
- WQAHSJDJDSDHEK-UHFFFAOYSA-N 3-(hydroxymethyl)-6-iodo-3-methylsulfinyl-2h-chromen-4-one Chemical compound C1=C(I)C=C2C(=O)C(S(=O)C)(CO)COC2=C1 WQAHSJDJDSDHEK-UHFFFAOYSA-N 0.000 claims description 2
- LBZJBUAELVDKDD-UHFFFAOYSA-N 3-(hydroxymethyl)-6-methoxy-3-methylsulfinyl-2h-chromen-4-one Chemical compound O1CC(CO)(S(C)=O)C(=O)C2=CC(OC)=CC=C21 LBZJBUAELVDKDD-UHFFFAOYSA-N 0.000 claims description 2
- NUOUTAPPXWAOCT-UHFFFAOYSA-N 3-(hydroxymethyl)-6-methoxychromen-4-one Chemical compound O1C=C(CO)C(=O)C2=CC(OC)=CC=C21 NUOUTAPPXWAOCT-UHFFFAOYSA-N 0.000 claims description 2
- XMEGTDONORZATC-UHFFFAOYSA-N 6-bromo-3-(hydroxymethyl)-3-methylsulfinyl-2h-chromen-4-one Chemical compound C1=C(Br)C=C2C(=O)C(S(=O)C)(CO)COC2=C1 XMEGTDONORZATC-UHFFFAOYSA-N 0.000 claims description 2
- FYUAHDSGRKWFKZ-UHFFFAOYSA-N 6-bromo-3-(hydroxymethyl)chromen-4-one Chemical compound C1=C(Br)C=C2C(=O)C(CO)=COC2=C1 FYUAHDSGRKWFKZ-UHFFFAOYSA-N 0.000 claims description 2
- FSYIQSXCGWFEJA-UHFFFAOYSA-N 6-chloro-3-(hydroxymethyl)-3-methylsulfinyl-2H-chromen-4-one Chemical compound ClC=1C=C2C(C(COC2=CC1)(S(=O)C)CO)=O FSYIQSXCGWFEJA-UHFFFAOYSA-N 0.000 claims description 2
- GFACKWBLCJLGSD-UHFFFAOYSA-N 6-hydroxy-3-(hydroxymethyl)chromen-4-one Chemical compound C1=C(O)C=C2C(=O)C(CO)=COC2=C1 GFACKWBLCJLGSD-UHFFFAOYSA-N 0.000 claims description 2
- OHTQNLINYBUWOF-UHFFFAOYSA-N 7-chloro-3-(hydroxymethyl)chromen-4-one Chemical compound ClC1=CC=C2C(=O)C(CO)=COC2=C1 OHTQNLINYBUWOF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- WZVUQCBAPFQEAA-UHFFFAOYSA-N 3-(hydroxymethyl)-6-iodochromen-4-one Chemical compound C1=C(I)C=C2C(=O)C(CO)=COC2=C1 WZVUQCBAPFQEAA-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- JJLDSEURXVLQMK-UHFFFAOYSA-N 3-(hydroxymethyl)-8-methoxychromen-4-one Chemical compound O1C=C(CO)C(=O)C2=C1C(OC)=CC=C2 JJLDSEURXVLQMK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SSPCJMUSQOMVOJ-UHFFFAOYSA-N 3-(hydroxymethyl)-8-propan-2-ylchromen-4-one Chemical compound O1C=C(CO)C(=O)C2=C1C(C(C)C)=CC=C2 SSPCJMUSQOMVOJ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- OCFNGYKLPMGLNU-UHFFFAOYSA-N 1-(2-hydroxy-5-methoxyphenyl)-2-methylsulfinylethanone Chemical compound COC1=CC=C(O)C(C(=O)CS(C)=O)=C1 OCFNGYKLPMGLNU-UHFFFAOYSA-N 0.000 description 1
- FWLIEUDMZIYEAW-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-2-methylsulfinylethanone Chemical compound CS(=O)CC(=O)C1=CC=CC=C1O FWLIEUDMZIYEAW-UHFFFAOYSA-N 0.000 description 1
- YWFOQTJJYWFRHC-UHFFFAOYSA-N 1-(5-bromo-2-hydroxyphenyl)-2-methylsulfinylethanone Chemical compound CS(=O)CC(=O)C1=CC(Br)=CC=C1O YWFOQTJJYWFRHC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010027654 Allergic conditions Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 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
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11276571A | 1971-02-04 | 1971-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2204051A1 true DE2204051A1 (de) | 1972-08-10 |
Family
ID=22345725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722204051 Pending DE2204051A1 (de) | 1971-02-04 | 1972-01-28 | 3 (Hydroxymethyl)-chromone und Verfahren zu ihrer Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4932861B1 (enExample) |
| AU (1) | AU459499B2 (enExample) |
| DE (1) | DE2204051A1 (enExample) |
| FR (1) | FR2124427A1 (enExample) |
| GB (1) | GB1319041A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2828196A1 (fr) * | 2001-08-03 | 2003-02-07 | Aventis Cropscience Sa | Derives de chromone a action fongicide, procede de preparation et application dans le domaine de l'agriculture |
-
1972
- 1972-01-14 GB GB185772A patent/GB1319041A/en not_active Expired
- 1972-01-27 AU AU38407/72A patent/AU459499B2/en not_active Expired
- 1972-01-28 DE DE19722204051 patent/DE2204051A1/de active Pending
- 1972-02-01 JP JP47011029A patent/JPS4932861B1/ja active Pending
- 1972-02-03 FR FR7203572A patent/FR2124427A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2124427A1 (enExample) | 1972-09-22 |
| GB1319041A (en) | 1973-05-31 |
| JPS4932861B1 (enExample) | 1974-09-03 |
| AU459499B2 (en) | 1975-03-27 |
| AU3840772A (en) | 1973-08-02 |
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