CH617435A5 - Process for the preparation of novel 5,5,7,7-tetramethylfuro-[3,4e]as-triazine-4-oxides and their use - Google Patents
Process for the preparation of novel 5,5,7,7-tetramethylfuro-[3,4e]as-triazine-4-oxides and their use Download PDFInfo
- Publication number
- CH617435A5 CH617435A5 CH514275A CH514275A CH617435A5 CH 617435 A5 CH617435 A5 CH 617435A5 CH 514275 A CH514275 A CH 514275A CH 514275 A CH514275 A CH 514275A CH 617435 A5 CH617435 A5 CH 617435A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- formula
- triazine
- substituents
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- RXJWBJGNIOZICN-UHFFFAOYSA-N 5,5,7,7-tetramethyl-3-(3-nitrophenyl)-4-oxidofuro[3,4-e][1,2,4]triazin-4-ium Chemical compound CC1(C)OC(C)(C)C([N+]=2[O-])=C1N=NC=2C1=CC=CC([N+]([O-])=O)=C1 RXJWBJGNIOZICN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- -1 benzene or toluene Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- BBQNHTWKPXQENB-UHFFFAOYSA-N 5,5,7,7-tetramethyl-4-oxido-3-phenylfuro[3,4-e][1,2,4]triazin-4-ium Chemical compound CC1(C)OC(C)(C)C([N+]=2[O-])=C1N=NC=2C1=CC=CC=C1 BBQNHTWKPXQENB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-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 compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PNKOBWIVJXIWKX-UHFFFAOYSA-N 4-oxidofuro[3,4-e][1,2,4]triazin-4-ium Chemical compound N1=NC=[N+](C=2C1=COC=2)[O-] PNKOBWIVJXIWKX-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VRDJHWPWOGKRMU-UHFFFAOYSA-N N-(4-hydrazinylidene-2,2,5,5-tetramethyloxolan-3-ylidene)hydroxylamine Chemical compound CC1(C)OC(C)(C)C(=NO)C1=NN VRDJHWPWOGKRMU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- FGGUAEKPLDMWSF-HMHFYOQSSA-N chembl2376821 Chemical compound O([C@@H]1[C@@H]2[C@@H]3O[C@]3(CO)[C@@H](O)[C@@]3(O)[C@H]([C@]2([C@H](C)C[C@@]1(O1)C(C)=C)O2)C[C@@H]([C@@H]3O)C)C21C1=CC=CC=C1 FGGUAEKPLDMWSF-HMHFYOQSSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-O nitrosooxidanium Chemical compound [OH2+]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-O 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 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
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46575974A | 1974-05-01 | 1974-05-01 | |
| US49657874A | 1974-08-12 | 1974-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617435A5 true CH617435A5 (en) | 1980-05-30 |
Family
ID=27041399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH514275A CH617435A5 (en) | 1974-05-01 | 1975-04-22 | Process for the preparation of novel 5,5,7,7-tetramethylfuro-[3,4e]as-triazine-4-oxides and their use |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS50149696A (en)) |
| AT (1) | AT357545B (en)) |
| BE (1) | BE828548A (en)) |
| CA (1) | CA1033734A (en)) |
| CH (1) | CH617435A5 (en)) |
| DD (1) | DD119792A5 (en)) |
| DE (1) | DE2517994A1 (en)) |
| DK (1) | DK139301B (en)) |
| ES (3) | ES437214A1 (en)) |
| FI (1) | FI57416C (en)) |
| FR (1) | FR2269347B1 (en)) |
| GB (1) | GB1496709A (en)) |
| HU (1) | HU171171B (en)) |
| IL (2) | IL47192A (en)) |
| NL (1) | NL7504919A (en)) |
| NO (1) | NO751455L (en)) |
| SE (1) | SE7504692L (en)) |
| SU (1) | SU588919A3 (en)) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI62837C (fi) * | 1977-03-18 | 1983-03-10 | Sandoz Ag | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyrano(4,3-e)-as-triaziner och deras 4-oxider |
| CH644863A5 (de) * | 1978-02-03 | 1984-08-31 | Sandoz Ag | Aethanopyrano-(4,3-e)-as-triazine, ihre herstellung und diese enthaltende beruhigungs- und schlafeinleitungsmittel. |
-
1975
- 1975-04-22 DK DK172775AA patent/DK139301B/da active IP Right Grant
- 1975-04-22 CH CH514275A patent/CH617435A5/de not_active IP Right Cessation
- 1975-04-22 FI FI751205A patent/FI57416C/fi not_active IP Right Cessation
- 1975-04-23 SE SE7504692A patent/SE7504692L/xx unknown
- 1975-04-23 DE DE19752517994 patent/DE2517994A1/de not_active Withdrawn
- 1975-04-23 NO NO751455A patent/NO751455L/no unknown
- 1975-04-25 NL NL7504919A patent/NL7504919A/xx not_active Application Discontinuation
- 1975-04-28 GB GB17647/75A patent/GB1496709A/en not_active Expired
- 1975-04-29 DD DD185757A patent/DD119792A5/xx unknown
- 1975-04-29 HU HU75SA00002784A patent/HU171171B/hu unknown
- 1975-04-29 IL IL47192A patent/IL47192A/xx unknown
- 1975-04-29 ES ES437214A patent/ES437214A1/es not_active Expired
- 1975-04-29 BE BE155916A patent/BE828548A/fr unknown
- 1975-04-30 CA CA225,868A patent/CA1033734A/en not_active Expired
- 1975-04-30 FR FR7513539A patent/FR2269347B1/fr not_active Expired
- 1975-04-30 AT AT332475A patent/AT357545B/de not_active IP Right Cessation
- 1975-04-30 JP JP50051568A patent/JPS50149696A/ja active Pending
-
1976
- 1976-03-05 SU SU762331170A patent/SU588919A3/ru active
- 1976-12-16 ES ES454312A patent/ES454312A1/es not_active Expired
- 1976-12-16 ES ES454313A patent/ES454313A1/es not_active Expired
-
1977
- 1977-08-17 IL IL52763A patent/IL52763A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1033734A (en) | 1978-06-27 |
| ES437214A1 (es) | 1977-05-16 |
| IL47192A0 (en) | 1975-07-28 |
| FR2269347A1 (en)) | 1975-11-28 |
| FI57416C (fi) | 1980-08-11 |
| NO751455L (en)) | 1975-11-04 |
| HU171171B (hu) | 1977-11-28 |
| FI57416B (fi) | 1980-04-30 |
| IL47192A (en) | 1978-04-30 |
| IL52763A0 (en) | 1977-10-31 |
| ES454313A1 (es) | 1977-12-01 |
| SE7504692L (sv) | 1975-11-03 |
| ES454312A1 (es) | 1977-12-01 |
| FI751205A7 (en)) | 1975-11-02 |
| AT357545B (de) | 1980-07-10 |
| DD119792A5 (en)) | 1976-05-12 |
| DK172775A (en)) | 1975-11-02 |
| BE828548A (fr) | 1975-10-29 |
| FR2269347B1 (en)) | 1978-08-18 |
| DE2517994A1 (de) | 1975-11-13 |
| AU8064075A (en) | 1976-11-04 |
| ATA332475A (de) | 1979-12-15 |
| JPS50149696A (en)) | 1975-11-29 |
| NL7504919A (nl) | 1975-11-04 |
| DK139301B (da) | 1979-01-29 |
| SU588919A3 (ru) | 1978-01-15 |
| DK139301C (en)) | 1979-07-02 |
| GB1496709A (en) | 1977-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PLX | Patent declared invalid from date of grant onwards |