DE2247828A1 - Sulfamoyl-anthranilsaeuren und verfahren zu ihrer herstellung - Google Patents
Sulfamoyl-anthranilsaeuren und verfahren zu ihrer herstellungInfo
- Publication number
- DE2247828A1 DE2247828A1 DE19722247828 DE2247828A DE2247828A1 DE 2247828 A1 DE2247828 A1 DE 2247828A1 DE 19722247828 DE19722247828 DE 19722247828 DE 2247828 A DE2247828 A DE 2247828A DE 2247828 A1 DE2247828 A1 DE 2247828A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- alcohol
- anthranilic acid
- furylmethyl
- cooh
- 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 13
- 238000004519 manufacturing process Methods 0.000 title claims 2
- -1 SULFAMOYL Chemical class 0.000 title description 27
- 239000002253 acid Substances 0.000 title description 4
- 150000007513 acids Chemical class 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000001882 diuretic effect Effects 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 208000004880 Polyuria Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- OAZOBYBYAKXURF-UHFFFAOYSA-N 2-(sulfamoylamino)benzoic acid Chemical class NS(=O)(=O)NC1=CC=CC=C1C(O)=O OAZOBYBYAKXURF-UHFFFAOYSA-N 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- CCFAKBRKTKVJPO-UHFFFAOYSA-N 1-anthroic acid Chemical class C1=CC=C2C=C3C(C(=O)O)=CC=CC3=CC2=C1 CCFAKBRKTKVJPO-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 24
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 5
- 229960003883 furosemide Drugs 0.000 description 5
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 230000000894 saliuretic effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LRBLIMZJQFWDLI-UHFFFAOYSA-N 2-(furan-2-ylmethylamino)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound C1=C(OC=2C=CC=CC=2)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 LRBLIMZJQFWDLI-UHFFFAOYSA-N 0.000 description 1
- FMUNLWXBVNIMFF-UHFFFAOYSA-N 4-chloro-2-(furan-2-ylmethylamino)-5-(hexoxymethylsulfamoyl)benzoic acid Chemical compound C(C1=CC=CO1)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(NCOCCCCCC)(=O)=O FMUNLWXBVNIMFF-UHFFFAOYSA-N 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical group C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 1
- 229960003602 guanethidine Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002474 hydralazine Drugs 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722247828 DE2247828A1 (de) | 1972-09-29 | 1972-09-29 | Sulfamoyl-anthranilsaeuren und verfahren zu ihrer herstellung |
| ES419012A ES419012A1 (es) | 1972-09-29 | 1973-09-24 | Procedimiento para la preparacion de derivados de acido an-tranilico. |
| NL7313123A NL7313123A (https=) | 1972-09-29 | 1973-09-24 | |
| IL43313A IL43313A0 (en) | 1972-09-29 | 1973-09-25 | Sulfamoyl anthranilic acids and process for their manufacture |
| AU60781/73A AU6078173A (en) | 1972-09-29 | 1973-09-27 | Sulfamoyl anthranilic acids and process for their manufactur |
| JP48109175A JPS4970958A (https=) | 1972-09-29 | 1973-09-28 | |
| AT835473A AT327881B (de) | 1972-09-29 | 1973-09-28 | Verfahren zur herstellung neuer furanderivate |
| ZA737654*A ZA737654B (en) | 1972-09-29 | 1973-09-28 | Sulfamoyl anthranilic acids and process for their manufacture |
| FR7334977A FR2201096A1 (en) | 1972-09-29 | 1973-10-01 | 5-Alkoxymethyl sulphamoyl-anthranilic acid derivs - diuretics and salure-tics from corresp 5-sulphamoyl-cpds with formaldehyde and alcohols |
| BE136227A BE805527A (fr) | 1972-09-29 | 1973-10-01 | Acides sulfamoyl anthraniliques, leur procede de preparation et leurs applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722247828 DE2247828A1 (de) | 1972-09-29 | 1972-09-29 | Sulfamoyl-anthranilsaeuren und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2247828A1 true DE2247828A1 (de) | 1974-04-04 |
Family
ID=5857758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722247828 Pending DE2247828A1 (de) | 1972-09-29 | 1972-09-29 | Sulfamoyl-anthranilsaeuren und verfahren zu ihrer herstellung |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4970958A (https=) |
| AT (1) | AT327881B (https=) |
| AU (1) | AU6078173A (https=) |
| BE (1) | BE805527A (https=) |
| DE (1) | DE2247828A1 (https=) |
| ES (1) | ES419012A1 (https=) |
| FR (1) | FR2201096A1 (https=) |
| IL (1) | IL43313A0 (https=) |
| NL (1) | NL7313123A (https=) |
| ZA (1) | ZA737654B (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4161533A (en) * | 1977-04-28 | 1979-07-17 | Hoechst Aktiengesellschaft | 5-Sulfamoyl-orthanilic acids and process for their preparation |
| EP0324988A1 (de) * | 1987-12-30 | 1989-07-26 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | 4-Chlor-3-sulfamoyl-benzoesäure-hydrazide, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittelpräparate und Verwendung der neuen Verbindungen zur Herstellung von diuretischen und salzentziehend wirkenden Arzneimittelpräparaten |
| WO2005082350A1 (en) * | 2004-02-20 | 2005-09-09 | Aventis Pharmaceuticals Inc. | Furosemide derivatives as modulators of hm74 and their use for the treatment of inflammation |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2302101A1 (fr) * | 1975-02-27 | 1976-09-24 | Joullie International Sa | Nouveaux derives de l'acide chloro-4 |
-
1972
- 1972-09-29 DE DE19722247828 patent/DE2247828A1/de active Pending
-
1973
- 1973-09-24 ES ES419012A patent/ES419012A1/es not_active Expired
- 1973-09-24 NL NL7313123A patent/NL7313123A/xx unknown
- 1973-09-25 IL IL43313A patent/IL43313A0/xx unknown
- 1973-09-27 AU AU60781/73A patent/AU6078173A/en not_active Expired
- 1973-09-28 JP JP48109175A patent/JPS4970958A/ja active Pending
- 1973-09-28 ZA ZA737654*A patent/ZA737654B/xx unknown
- 1973-09-28 AT AT835473A patent/AT327881B/de not_active IP Right Cessation
- 1973-10-01 FR FR7334977A patent/FR2201096A1/fr active Granted
- 1973-10-01 BE BE136227A patent/BE805527A/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4161533A (en) * | 1977-04-28 | 1979-07-17 | Hoechst Aktiengesellschaft | 5-Sulfamoyl-orthanilic acids and process for their preparation |
| DE2718871C3 (de) | 1977-04-28 | 1980-07-17 | Hoechst Ag, 6000 Frankfurt | N-(2-Furylmethyl)-5-sulfamoylorthanilsäuren und deren physiologisch verträgliche Salze und Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Oedemkrankheiten und Bluthochdruck |
| EP0324988A1 (de) * | 1987-12-30 | 1989-07-26 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | 4-Chlor-3-sulfamoyl-benzoesäure-hydrazide, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittelpräparate und Verwendung der neuen Verbindungen zur Herstellung von diuretischen und salzentziehend wirkenden Arzneimittelpräparaten |
| WO2005082350A1 (en) * | 2004-02-20 | 2005-09-09 | Aventis Pharmaceuticals Inc. | Furosemide derivatives as modulators of hm74 and their use for the treatment of inflammation |
| US7232811B2 (en) | 2004-02-20 | 2007-06-19 | Aventis Pharmaceuticals Inc. | Furosemide modulators of HM74 |
| US7556931B2 (en) | 2004-02-20 | 2009-07-07 | Aventis Pharmaceuticals Inc. | Furosemide modulators of HM74 |
| AU2005216879B2 (en) * | 2004-02-20 | 2009-12-10 | Aventis Pharmaceuticals Inc | Furosemide derivatives as modulators of HM74 and their use for the treatment of inflammation |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA835473A (de) | 1975-05-15 |
| FR2201096B1 (https=) | 1977-04-15 |
| FR2201096A1 (en) | 1974-04-26 |
| JPS4970958A (https=) | 1974-07-09 |
| AT327881B (de) | 1976-02-25 |
| NL7313123A (https=) | 1974-04-02 |
| IL43313A0 (en) | 1973-11-28 |
| ES419012A1 (es) | 1976-03-16 |
| BE805527A (fr) | 1974-04-01 |
| ZA737654B (en) | 1974-08-28 |
| AU6078173A (en) | 1975-03-27 |
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