DE2439137A1 - 3-methyl-pyrazol-5-carboxylate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate - Google Patents
3-methyl-pyrazol-5-carboxylate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparateInfo
- Publication number
- DE2439137A1 DE2439137A1 DE2439137A DE2439137A DE2439137A1 DE 2439137 A1 DE2439137 A1 DE 2439137A1 DE 2439137 A DE2439137 A DE 2439137A DE 2439137 A DE2439137 A DE 2439137A DE 2439137 A1 DE2439137 A1 DE 2439137A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- pyrazole
- carboxylate
- amino
- weight
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 7
- WSMQKESQZFQMFW-UHFFFAOYSA-N 5-methyl-pyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1 WSMQKESQZFQMFW-UHFFFAOYSA-N 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002904 solvent Substances 0.000 claims description 13
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical class O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims 1
- FNHVVMJBCILJGA-UHFFFAOYSA-N 4-methyl-pyrazole-3-carboxylic acid Chemical compound CC=1C=NNC=1C(O)=O FNHVVMJBCILJGA-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 241001465754 Metazoa Species 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 230000037396 body weight Effects 0.000 description 17
- 241000700159 Rattus Species 0.000 description 16
- 150000003626 triacylglycerols Chemical class 0.000 description 15
- 210000002966 serum Anatomy 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
- 235000021588 free fatty acids Nutrition 0.000 description 10
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 238000003304 gavage Methods 0.000 description 7
- 235000003642 hunger Nutrition 0.000 description 7
- 230000002147 killing effect Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000002784 stomach Anatomy 0.000 description 6
- 206010002091 Anaesthesia Diseases 0.000 description 5
- 230000037005 anaesthesia Effects 0.000 description 5
- 238000012754 cardiac puncture Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 230000004130 lipolysis Effects 0.000 description 5
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 238000009838 combustion analysis Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- WTGCVDANJVGUCN-UHFFFAOYSA-N 3-methylpyrazole-3-carboxylic acid Chemical compound OC(=O)C1(C)C=CN=N1 WTGCVDANJVGUCN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- -1 Alkyl radicals Chemical class 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 238000010241 blood sampling Methods 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 1
- WCQYJWRMYFJLRQ-UHFFFAOYSA-N 5-ethyl-1h-pyrazole-3-carboxylic acid Chemical compound CCC1=CC(C(O)=O)=NN1 WCQYJWRMYFJLRQ-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 206010043087 Tachyphylaxis Diseases 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ORUCTBNNYKZMSK-UHFFFAOYSA-N methyl 1h-pyrazole-5-carboxylate Chemical compound COC(=O)C=1C=CNN=1 ORUCTBNNYKZMSK-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 230000002129 tachyphylactic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2439137A DE2439137A1 (de) | 1974-08-14 | 1974-08-14 | 3-methyl-pyrazol-5-carboxylate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
| FI752070A FI752070A7 (enExample) | 1974-08-14 | 1975-07-17 | |
| CA231,779A CA1062258A (en) | 1974-08-14 | 1975-07-18 | 3-methyl-pyrazole-5-carboxylates and a process for their production |
| US05/601,316 US3980646A (en) | 1974-08-14 | 1975-08-01 | 3-Methylpyrazole-5-carboxylates and medicaments containing these compounds |
| AT618075A AT338287B (de) | 1974-08-14 | 1975-08-08 | Verfahren zur herstellung von neuen 7- (3'-amino-2'-hydroxypropyl)-theophyllin-3-methylpyrazol-5-carboxylaten |
| GB33528/75A GB1481147A (en) | 1974-08-14 | 1975-08-12 | 3-methyl-pyrazole-5-carboxylates |
| JP50099048A JPS51104019A (en) | 1974-08-14 | 1975-08-12 | 33 mechirupirazooru 55 karubonsanenruino seiho |
| BE159165A BE832389A (fr) | 1974-08-14 | 1975-08-13 | 3-methyl-pyrazole-5-carboxylates, procede pour leur fabrication et preparation pharmaceutiques contenant ces composes |
| FR7525251A FR2281758A1 (fr) | 1974-08-14 | 1975-08-13 | 3-methyl-pyrazole-5-carboxylates, procede pour leur fabrication et preparations pharmaceutiques contenant ces composes |
| AR259984A AR211100A1 (es) | 1974-08-14 | 1975-08-13 | Procedimiento para la preparacion de 3-metilpirazol-5-carboxilatos. |
| NL7509706A NL7509706A (nl) | 1974-08-14 | 1975-08-14 | 3-methylpyrazool-5-carboxylaten, werkwijze voor het bereiden ervan en deze verbindingen bevatten- de geneesmiddelpreparaten. |
| SE7509123A SE7509123L (sv) | 1974-08-14 | 1975-08-14 | 3-metylpyrazol-5-karboxylat, sett att framstella desamma och lekemedelpreparat innehallande desamma. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2439137A DE2439137A1 (de) | 1974-08-14 | 1974-08-14 | 3-methyl-pyrazol-5-carboxylate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2439137A1 true DE2439137A1 (de) | 1976-08-12 |
Family
ID=5923236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2439137A Withdrawn DE2439137A1 (de) | 1974-08-14 | 1974-08-14 | 3-methyl-pyrazol-5-carboxylate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3980646A (enExample) |
| JP (1) | JPS51104019A (enExample) |
| AR (1) | AR211100A1 (enExample) |
| AT (1) | AT338287B (enExample) |
| BE (1) | BE832389A (enExample) |
| CA (1) | CA1062258A (enExample) |
| DE (1) | DE2439137A1 (enExample) |
| FI (1) | FI752070A7 (enExample) |
| FR (1) | FR2281758A1 (enExample) |
| GB (1) | GB1481147A (enExample) |
| NL (1) | NL7509706A (enExample) |
| SE (1) | SE7509123L (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4092417A (en) * | 1976-12-08 | 1978-05-30 | Johann A. Wulfing | Theophylline salts of 5-methylisoxazole-3-carboxylic acid |
| FR2373283A1 (fr) * | 1976-12-10 | 1978-07-07 | Wuelfing Johann A | Composes derives de l'isoxazole, utilisables comme medicament |
| CA2501134A1 (en) * | 2002-10-10 | 2004-04-22 | Arena Pharmaceuticals, Inc. | 5-substituted 2h-pyrazole-3-carboxylic acid derivatives as antilipolytic agents for the treatment of metabolic-related disorders such as dyslipidemia |
| WO2005011677A1 (en) * | 2003-06-13 | 2005-02-10 | Arena Pharmaceuticals, Inc. | 5-substituted 2h-pyrazole-3-carboxylic acid derivatives as agonists for the nicotinic acid receptor rup25 for the treatment of dyslipidemia and related diseases |
| JP4348440B2 (ja) | 2005-09-01 | 2009-10-21 | 有洙 安 | 透過性補強材と発泡体を利用したベッド用マットレス及びその製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2924598A (en) * | 1960-02-09 | Methods of preparing same | ||
| DE1089763B (de) * | 1957-10-26 | 1960-09-29 | Wuelfing J A Fa | Verfahren zur Herstellung des 7-[ª‰-Oxy-ª†-(methyl-ª‰-oxyaethylamino)-propyl]-theophyllin-nikotinats |
| DE1102750B (de) * | 1958-07-17 | 1961-03-23 | Wuelfing J A Fa | Verfahren zur Herstellung eines Salzes von Theophyllinbasen |
| US3728346A (en) * | 1971-07-16 | 1973-04-17 | Degussa | Hydroxyphenylhydroxyalkylaminoalkyltheophyllines |
| AT313916B (de) * | 1971-10-28 | 1974-03-11 | Degussa | Verfahren zur Herstellung von neuen basisch substituierten Theophyllinen und deren Säureadditionssalzen |
-
1974
- 1974-08-14 DE DE2439137A patent/DE2439137A1/de not_active Withdrawn
-
1975
- 1975-07-17 FI FI752070A patent/FI752070A7/fi not_active Application Discontinuation
- 1975-07-18 CA CA231,779A patent/CA1062258A/en not_active Expired
- 1975-08-01 US US05/601,316 patent/US3980646A/en not_active Expired - Lifetime
- 1975-08-08 AT AT618075A patent/AT338287B/de not_active IP Right Cessation
- 1975-08-12 GB GB33528/75A patent/GB1481147A/en not_active Expired
- 1975-08-12 JP JP50099048A patent/JPS51104019A/ja active Pending
- 1975-08-13 BE BE159165A patent/BE832389A/xx unknown
- 1975-08-13 AR AR259984A patent/AR211100A1/es active
- 1975-08-13 FR FR7525251A patent/FR2281758A1/fr active Granted
- 1975-08-14 SE SE7509123A patent/SE7509123L/xx unknown
- 1975-08-14 NL NL7509706A patent/NL7509706A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA618075A (de) | 1976-12-15 |
| CA1062258A (en) | 1979-09-11 |
| FR2281758A1 (fr) | 1976-03-12 |
| US3980646A (en) | 1976-09-14 |
| AT338287B (de) | 1977-08-10 |
| BE832389A (fr) | 1976-02-13 |
| FR2281758B1 (enExample) | 1978-09-08 |
| FI752070A7 (enExample) | 1976-02-15 |
| AR211100A1 (es) | 1977-10-31 |
| SE7509123L (sv) | 1976-02-16 |
| GB1481147A (en) | 1977-07-27 |
| NL7509706A (nl) | 1976-02-17 |
| JPS51104019A (en) | 1976-09-14 |
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| AT271742B (de) | Verfahren zur Herstellung von neuen N-substituierten Noratropiniumsalzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |