DE3438244A1 - 4-chlor-furo-(3,4-c)-pyridinderivate, verfahren zu ihrer herstellung und arzneimittel mit einem gehalt an diesen verbindungen - Google Patents
4-chlor-furo-(3,4-c)-pyridinderivate, verfahren zu ihrer herstellung und arzneimittel mit einem gehalt an diesen verbindungenInfo
- Publication number
- DE3438244A1 DE3438244A1 DE19843438244 DE3438244A DE3438244A1 DE 3438244 A1 DE3438244 A1 DE 3438244A1 DE 19843438244 DE19843438244 DE 19843438244 DE 3438244 A DE3438244 A DE 3438244A DE 3438244 A1 DE3438244 A1 DE 3438244A1
- Authority
- DE
- Germany
- Prior art keywords
- furo
- dihydro
- hydroxy
- radicals
- carbon atoms
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 26
- 229940126601 medicinal product Drugs 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical class N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 claims description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- GFEZPGADIMGWOH-UHFFFAOYSA-N 6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical class CC1=NC=C2COCC2=C1O GFEZPGADIMGWOH-UHFFFAOYSA-N 0.000 claims 2
- 102100033070 Histone acetyltransferase KAT6B Human genes 0.000 claims 2
- 101000944174 Homo sapiens Histone acetyltransferase KAT6B Proteins 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 2,3-dichlorophenyl Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000035619 diuresis Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- GJVNMIQVQXYJCP-UHFFFAOYSA-N furo[3,4-c]pyridine Chemical compound C1=NC=CC2=[C]OC=C21 GJVNMIQVQXYJCP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 description 2
- 229960000356 tienilic acid Drugs 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- KRFFDJKRFIRFEH-UHFFFAOYSA-N 3,3,6-trimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound CC1=NC=C2C(C)(C)OCC2=C1O KRFFDJKRFIRFEH-UHFFFAOYSA-N 0.000 description 1
- WPRNMWVODLENAP-UHFFFAOYSA-N 3,6-dimethyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(C)OC2 WPRNMWVODLENAP-UHFFFAOYSA-N 0.000 description 1
- VFROHEFJKCMRAI-UHFFFAOYSA-N 3,6-dimethyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C)C1=CC=CC=C1 VFROHEFJKCMRAI-UHFFFAOYSA-N 0.000 description 1
- CZOLAEVRQAMQJD-UHFFFAOYSA-N 4-chloro-3,6-dimethyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound ClC1=NC(C)=C(O)C2=C1C(C)OC2 CZOLAEVRQAMQJD-UHFFFAOYSA-N 0.000 description 1
- BJJGWGOGOMEECW-UHFFFAOYSA-N 4-chloro-3-(2,3-dichlorophenyl)-6-methyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC(Cl)=C2C=1COC2(C=1C(=C(Cl)C=CC=1)Cl)C1=CC=CC=C1 BJJGWGOGOMEECW-UHFFFAOYSA-N 0.000 description 1
- HBLJSMREXQKFNU-UHFFFAOYSA-N 6-methyl-3,3-diphenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C=1C=CC=CC=1)C1=CC=CC=C1 HBLJSMREXQKFNU-UHFFFAOYSA-N 0.000 description 1
- AXZNOBIHGUZGPG-UHFFFAOYSA-N 6-methyl-3-(2-phenylethyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC=C2C1CCC1=CC=CC=C1 AXZNOBIHGUZGPG-UHFFFAOYSA-N 0.000 description 1
- AWSNANLRLHTJCZ-UHFFFAOYSA-N 6-methyl-3-phenyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC=C2C1C1=CC=CC=C1 AWSNANLRLHTJCZ-UHFFFAOYSA-N 0.000 description 1
- VABUPDWURAFFTL-UHFFFAOYSA-N 6-methyl-3-propyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(CCC)OC2 VABUPDWURAFFTL-UHFFFAOYSA-N 0.000 description 1
- ARIQBLIVTNQIKZ-UHFFFAOYSA-N C12=C(O)C(C)=NC=C2C(C=2C=CC(Cl)=CC=2)OC1C(C=1)=CC=CC=1OCCN1CCCC1 Chemical compound C12=C(O)C(C)=NC=C2C(C=2C=CC(Cl)=CC=2)OC1C(C=1)=CC=CC=1OCCN1CCCC1 ARIQBLIVTNQIKZ-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838327817A GB8327817D0 (en) | 1983-10-18 | 1983-10-18 | 4-halo-furo-(3 4-c)-pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3438244A1 true DE3438244A1 (de) | 1985-04-25 |
| DE3438244C2 DE3438244C2 (en, 2012) | 1990-08-30 |
Family
ID=10550364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843438244 Granted DE3438244A1 (de) | 1983-10-18 | 1984-10-18 | 4-chlor-furo-(3,4-c)-pyridinderivate, verfahren zu ihrer herstellung und arzneimittel mit einem gehalt an diesen verbindungen |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4585776A (en, 2012) |
| JP (1) | JPS60104090A (en, 2012) |
| AT (1) | AT391699B (en, 2012) |
| BE (1) | BE900780A (en, 2012) |
| CA (1) | CA1257270A (en, 2012) |
| CH (1) | CH662118A5 (en, 2012) |
| DE (1) | DE3438244A1 (en, 2012) |
| DK (1) | DK158003C (en, 2012) |
| DZ (1) | DZ687A1 (en, 2012) |
| ES (1) | ES536814A0 (en, 2012) |
| FI (1) | FI80036C (en, 2012) |
| FR (2) | FR2553417B1 (en, 2012) |
| GB (2) | GB8327817D0 (en, 2012) |
| HK (1) | HK54787A (en, 2012) |
| IE (1) | IE58041B1 (en, 2012) |
| IT (1) | IT1176986B (en, 2012) |
| LU (1) | LU85583A1 (en, 2012) |
| MA (1) | MA20251A1 (en, 2012) |
| NL (1) | NL8403181A (en, 2012) |
| OA (1) | OA07840A (en, 2012) |
| PT (2) | PT79369B (en, 2012) |
| SE (1) | SE459093B (en, 2012) |
| SG (1) | SG25387G (en, 2012) |
| ZA (1) | ZA847961B (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4010657A1 (de) * | 1989-04-03 | 1990-10-04 | Scras | Trennung von isomeren von furo (3,4-c) pyridinderivaten |
| AT397093B (de) * | 1988-04-06 | 1994-01-25 | Sod Conseils Rech Applic | Stereospezifisches verfahren für die herstellung von enantiomeren des 3-substituierten furo (3,4-c) pyridins, so erhaltene enantiomere oder mischungen davon sowie diese enthaltene therapeutische mittel |
| DE4115681C2 (de) * | 1990-05-14 | 2003-10-30 | Sod Conseils Rech Applic | Verfahren zur Herstellung von Furo[3,4-c]pyridinderivaten in nicht racemischer Form |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8917168D0 (en) * | 1989-07-27 | 1989-09-13 | Scras | Asymmetric synthesis of furo(3,4-c)pyridine derivatives |
| US6865862B2 (en) * | 2000-11-20 | 2005-03-15 | C.G. Bretting Mfg. Co., Inc. | Log bander apparatus and method |
| GB0221494D0 (en) * | 2002-09-16 | 2002-10-23 | Generics Uk Ltd | Novel processes for the preparation of 1.3-dihydro-6-methylfuro (3,4-c) pyndin derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2850948A1 (de) * | 1977-11-25 | 1979-05-31 | Scras | Pyridinderivat, verfahren zu seiner herstellung und arzneimittel |
| DE3204596A1 (de) * | 1981-02-10 | 1982-09-09 | Société de Conseils de Recherches et d'Applications Scientifiques S.A., 75008 Paris | Furo-(3,4-c)-pyridinderivate, verfahren zu deren herstellung und diese enthaltende therapeutische zusammensetzung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5621578B2 (en, 2012) * | 1973-06-02 | 1981-05-20 | ||
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
-
1983
- 1983-10-18 GB GB838327817A patent/GB8327817D0/en active Pending
-
1984
- 1984-10-09 BE BE0/213802A patent/BE900780A/fr not_active IP Right Cessation
- 1984-10-10 CH CH4863/84A patent/CH662118A5/fr not_active IP Right Cessation
- 1984-10-10 LU LU85583A patent/LU85583A1/fr unknown
- 1984-10-11 GB GB08425704A patent/GB2148292B/en not_active Expired
- 1984-10-11 ZA ZA847961A patent/ZA847961B/xx unknown
- 1984-10-12 SE SE8405118A patent/SE459093B/sv not_active IP Right Cessation
- 1984-10-13 DZ DZ847301A patent/DZ687A1/fr active
- 1984-10-15 MA MA20475A patent/MA20251A1/fr unknown
- 1984-10-15 FI FI844034A patent/FI80036C/fi not_active IP Right Cessation
- 1984-10-16 US US06/661,376 patent/US4585776A/en not_active Expired - Lifetime
- 1984-10-17 JP JP59216483A patent/JPS60104090A/ja active Granted
- 1984-10-17 IE IE266384A patent/IE58041B1/en not_active IP Right Cessation
- 1984-10-17 DK DK495984A patent/DK158003C/da not_active IP Right Cessation
- 1984-10-17 PT PT79369A patent/PT79369B/pt not_active IP Right Cessation
- 1984-10-17 ES ES536814A patent/ES536814A0/es active Granted
- 1984-10-17 IT IT23176/84A patent/IT1176986B/it active
- 1984-10-18 OA OA58417A patent/OA07840A/xx unknown
- 1984-10-18 DE DE19843438244 patent/DE3438244A1/de active Granted
- 1984-10-18 AT AT0332984A patent/AT391699B/de not_active IP Right Cessation
- 1984-10-18 FR FR8415948A patent/FR2553417B1/fr not_active Expired
- 1984-10-18 FR FR8415947A patent/FR2553286B1/fr not_active Expired
- 1984-10-18 NL NL8403181A patent/NL8403181A/nl not_active Application Discontinuation
- 1984-10-18 CA CA000465804A patent/CA1257270A/en not_active Expired
- 1984-11-16 PT PT79512A patent/PT79512B/pt not_active IP Right Cessation
-
1987
- 1987-03-12 SG SG253/87A patent/SG25387G/en unknown
- 1987-07-23 HK HK547/87A patent/HK54787A/xx not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2850948A1 (de) * | 1977-11-25 | 1979-05-31 | Scras | Pyridinderivat, verfahren zu seiner herstellung und arzneimittel |
| DE3204596A1 (de) * | 1981-02-10 | 1982-09-09 | Société de Conseils de Recherches et d'Applications Scientifiques S.A., 75008 Paris | Furo-(3,4-c)-pyridinderivate, verfahren zu deren herstellung und diese enthaltende therapeutische zusammensetzung |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT397093B (de) * | 1988-04-06 | 1994-01-25 | Sod Conseils Rech Applic | Stereospezifisches verfahren für die herstellung von enantiomeren des 3-substituierten furo (3,4-c) pyridins, so erhaltene enantiomere oder mischungen davon sowie diese enthaltene therapeutische mittel |
| DE4010657A1 (de) * | 1989-04-03 | 1990-10-04 | Scras | Trennung von isomeren von furo (3,4-c) pyridinderivaten |
| DE4010657C2 (de) * | 1989-04-03 | 1999-01-28 | Sod Conseils Rech Applic | Verfahren zur Trennung der Stereoisomere von 7-Hydroxy-furo-[3,4-c]pyridinderivaten |
| DE4115681C2 (de) * | 1990-05-14 | 2003-10-30 | Sod Conseils Rech Applic | Verfahren zur Herstellung von Furo[3,4-c]pyridinderivaten in nicht racemischer Form |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1695556C3 (de) | 3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate | |
| DE2706977A1 (de) | Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung | |
| DE3412885A1 (de) | Fuoro-(3,4-c)-pyridin-derivate, verfahren zu ihrer herstellung und arzneimittel | |
| DD207718A5 (de) | Verfahren zur herstellung von 2-guanidino-4-heteroarylthiazolen | |
| DE2634433A1 (de) | Harnstoffderivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2123923B2 (en, 2012) | ||
| DE2604748A1 (de) | Aminoderivate von imidazo(4,5-b) pyridinen | |
| DE3439450A1 (de) | 1,2,4-triazolo-carbamate und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel | |
| DE2635961A1 (de) | Therapeutisch wirksame verbindungen und verfahren zu ihrer herstellung | |
| DE2921660A1 (de) | 5-nitroimidazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende antiprotozoen-mittel | |
| DE3438244A1 (de) | 4-chlor-furo-(3,4-c)-pyridinderivate, verfahren zu ihrer herstellung und arzneimittel mit einem gehalt an diesen verbindungen | |
| EP0177907B1 (de) | Neue 2-Pyridin-thiol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate | |
| DE1963317A1 (de) | Chemische Verfahren und Produkte | |
| DE2446100A1 (de) | Phenoxyalkancarbonsaeureamide von substituierten thiazolidincarbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln | |
| DE2609574C3 (de) | 1 -^-Fluor-S-trifluormethylthiophenyD-piperazin, dessen Salze, Verfahren zu dessen Herstellung und Arzneimittel | |
| DE3538063A1 (de) | 6-phenethylaminoalkyl-furo-(3,4-c)-pyridinderivate, verfahren zu deren herstellung und diese enthaltende therapeutische zusammensetzungen | |
| EP0037471B1 (de) | 1-Aroyl-2-phenylamino-2-imidazoline, ihre Herstellung und diese enthaltende Arzneimittel | |
| AT383806B (de) | Verfahren zur herstellung neuer verbindungen von furo-(3,4-c)-pyridinderivaten und von deren salzen | |
| DE3431195A1 (de) | Neue benzodiazepine, verfahren zu ihrer herstellung sowie ihre verwendung | |
| DE2433988C2 (de) | 2H(1)Benzopyrano- und 2H(1)Benzothiopyrano [4,3,2-cd] indazol-N-oxide, Verfahren zur ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE3310796A1 (de) | Substituierte ethenylderivate von 1h-pyrazolo-(1,5-a)-pyrimidin, verfahren zur herstellung derselben, sowie diese enthaltende pharmazeutische praeparate | |
| DE2610679C2 (de) | Sulfinylgruppenhaltige Oximätherderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE2002107A1 (de) | Neue organische Verbindungen und Verfahren zu deren Herstellung | |
| DE2334973A1 (de) | Neue biphenyl-derivate | |
| DE2607575A1 (de) | Triazolocycloalkylhydrothiadiazin- derivate, verfahren zu deren herstellung, sowie dieselben enthaltende pharmazeutische praeparate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |