CH495363A - Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden - Google Patents
Verfahren zur Herstellung von neuen antidiabetisch wirksamen SulfonamidenInfo
- Publication number
- CH495363A CH495363A CH1661467A CH1661467A CH495363A CH 495363 A CH495363 A CH 495363A CH 1661467 A CH1661467 A CH 1661467A CH 1661467 A CH1661467 A CH 1661467A CH 495363 A CH495363 A CH 495363A
- Authority
- CH
- Switzerland
- Prior art keywords
- aralkyl
- aryl
- optionally substituted
- alkyl
- benzenesulfonamide
- Prior art date
Links
- 230000003178 anti-diabetic effect Effects 0.000 title claims abstract description 5
- 150000003456 sulfonamides Chemical class 0.000 title claims description 4
- 239000003472 antidiabetic agent Substances 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- -1 aryl mercaptoalkyl Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 150000005006 2-aminopyrimidines Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 abstract description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 abstract description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 101000713585 Homo sapiens Tubulin beta-4A chain Proteins 0.000 description 14
- 102100036788 Tubulin beta-4A chain Human genes 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 101000713575 Homo sapiens Tubulin beta-3 chain Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 102100036790 Tubulin beta-3 chain Human genes 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- FNJBMURECUULDN-UHFFFAOYSA-N 4-methyl-5-(2-methylpropyl)pyrimidin-2-amine Chemical compound CC(C)CC1=CN=C(N)N=C1C FNJBMURECUULDN-UHFFFAOYSA-N 0.000 description 2
- KVHFWPDZSJYZNF-UHFFFAOYSA-N 4-methyl-5-propylpyrimidin-2-amine Chemical compound CCCC1=CN=C(N)N=C1C KVHFWPDZSJYZNF-UHFFFAOYSA-N 0.000 description 2
- AIOOBFYEASSZHV-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinazolin-2-amine Chemical compound C1CCCC2=NC(N)=NC=C21 AIOOBFYEASSZHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SMTCESWQPCUXFW-UHFFFAOYSA-N 4,5-diethylpyrimidin-2-amine Chemical compound NC1=NC=C(C(=N1)CC)CC SMTCESWQPCUXFW-UHFFFAOYSA-N 0.000 description 1
- OYLUXQLMIVJBKE-UHFFFAOYSA-N 4-(2-methylpropyl)pyrimidin-2-amine Chemical compound CC(C)CC1=CC=NC(N)=N1 OYLUXQLMIVJBKE-UHFFFAOYSA-N 0.000 description 1
- NLTFNXNWBRJIRZ-UHFFFAOYSA-N 4-methyl-5-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)C1=CN=C(N)N=C1C NLTFNXNWBRJIRZ-UHFFFAOYSA-N 0.000 description 1
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000005005 aminopyrimidines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HLBLNLYCFFWMFF-UHFFFAOYSA-N n-pyrimidin-2-ylbenzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NC1=NC=CC=N1 HLBLNLYCFFWMFF-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B08—CLEANING
- B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
- B08B1/00—Cleaning by methods involving the use of tools
- B08B1/10—Cleaning by methods involving the use of tools characterised by the type of cleaning tool
- B08B1/14—Wipes; Absorbent members, e.g. swabs or sponges
- B08B1/143—Wipes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1060270A CH508634A (de) | 1966-11-29 | 1967-11-27 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
| CH1060370A CH508635A (de) | 1966-11-29 | 1967-11-27 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0090051 | 1966-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH495363A true CH495363A (de) | 1970-08-31 |
Family
ID=6985090
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1661467A CH495363A (de) | 1966-11-29 | 1967-11-27 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
| CH1060170A CH533626A (de) | 1966-11-29 | 1967-11-27 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1060170A CH533626A (de) | 1966-11-29 | 1967-11-27 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3520887A (enExample) |
| AT (4) | AT278828B (enExample) |
| CH (2) | CH495363A (enExample) |
| DE (1) | DE1670168C3 (enExample) |
| FR (1) | FR1571294A (enExample) |
| GB (1) | GB1136190A (enExample) |
| GR (1) | GR38284B (enExample) |
| NL (1) | NL6716256A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627768A (en) * | 1969-06-24 | 1971-12-14 | Schering Ag | Isoxazolecarbonamidobenzene-sulfonamides |
| DE2048906A1 (de) * | 1970-10-06 | 1972-04-13 | Boehringer Mannheim Gmbh, 6800 Mannheim | Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung |
| DE2107557A1 (de) * | 1971-02-17 | 1972-10-05 | Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt | Benzolsulfonamidopyrimidine und Verfahren zu ihrer Herstellung |
| DE2152230A1 (de) * | 1971-10-20 | 1973-04-26 | Boehringer Mannheim Gmbh | Blutzuckersenkende sulfonylaminopyrimidine und verfahren zu deren herstellung |
| US4487626A (en) * | 1980-08-22 | 1984-12-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4651201A (en) * | 1984-06-01 | 1987-03-17 | Arnold Schoolman | Stereoscopic endoscope arrangement |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124597A (en) * | 1964-03-10 | |||
| BE622085A (enExample) * | 1961-01-26 | |||
| US3242174A (en) * | 1962-02-06 | 1966-03-22 | Pfizer & Co C | 1-(tertiary aminosulfonyl)-3-(hydrocarbon) ureas |
| GB1050373A (enExample) * | 1963-05-28 | |||
| DE1188589B (de) * | 1963-12-14 | 1965-03-11 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| NL129627C (enExample) * | 1964-05-20 | |||
| DE1545944A1 (de) * | 1964-06-19 | 1969-12-11 | Hoffmann La Roche | Verfahren zur Herstellung von neuen Sulfonamiden der Pyrimidinreihe |
-
1966
- 1966-11-29 DE DE1670168A patent/DE1670168C3/de not_active Expired
-
1967
- 1967-11-15 US US683130A patent/US3520887A/en not_active Expired - Lifetime
- 1967-11-27 CH CH1661467A patent/CH495363A/de not_active IP Right Cessation
- 1967-11-27 CH CH1060170A patent/CH533626A/de not_active IP Right Cessation
- 1967-11-27 GB GB53841/67A patent/GB1136190A/en not_active Expired
- 1967-11-27 GR GR670138284A patent/GR38284B/el unknown
- 1967-11-28 AT AT02795/69A patent/AT278828B/de not_active IP Right Cessation
- 1967-11-28 AT AT02794/69A patent/AT278827B/de not_active IP Right Cessation
- 1967-11-28 AT AT279669A patent/AT278829B/de not_active IP Right Cessation
- 1967-11-28 FR FR1571294D patent/FR1571294A/fr not_active Expired
- 1967-11-28 AT AT1074467A patent/AT278809B/de not_active IP Right Cessation
- 1967-11-29 NL NL6716256A patent/NL6716256A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR38284B (el) | 1969-10-17 |
| US3520887A (en) | 1970-07-21 |
| NL6716256A (enExample) | 1968-05-30 |
| CH533626A (de) | 1973-02-15 |
| DE1670168A1 (de) | 1972-03-02 |
| DE1670168B2 (de) | 1974-08-22 |
| AT278829B (de) | 1970-02-10 |
| FR1571294A (enExample) | 1969-06-20 |
| AT278828B (de) | 1970-02-10 |
| DE1670168C3 (de) | 1975-04-10 |
| AT278809B (de) | 1970-02-10 |
| AT278827B (de) | 1970-02-10 |
| GB1136190A (en) | 1968-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |