FI74461C - Foerfarande foer framstaellning av bensimidazolderivat med diuretisk och antihypertensiv verkan. - Google Patents
Foerfarande foer framstaellning av bensimidazolderivat med diuretisk och antihypertensiv verkan. Download PDFInfo
- Publication number
- FI74461C FI74461C FI791083A FI791083A FI74461C FI 74461 C FI74461 C FI 74461C FI 791083 A FI791083 A FI 791083A FI 791083 A FI791083 A FI 791083A FI 74461 C FI74461 C FI 74461C
- Authority
- FI
- Finland
- Prior art keywords
- chloro
- formula
- compound
- filtered
- och
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002934 diuretic Substances 0.000 claims description 6
- 230000001882 diuretic effect Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- NIIPOMKMZZUVKA-UHFFFAOYSA-N 1-cyano-1-methylguanidine Chemical compound N#CN(C)C(N)=N NIIPOMKMZZUVKA-UHFFFAOYSA-N 0.000 claims description 3
- -1 amino, guanidino, N-methylguanidino Chemical group 0.000 claims description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- JJWXBXFGEPDWQX-UHFFFAOYSA-N 4,5-diamino-2-chlorobenzenesulfonamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1N JJWXBXFGEPDWQX-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 5
- MUUQHCOAOLLHIL-UHFFFAOYSA-N n-(3-chlorophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(Cl)=C1 MUUQHCOAOLLHIL-UHFFFAOYSA-N 0.000 description 5
- YWANGSCDWBUSBK-UHFFFAOYSA-N n-(5-chloro-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1[N+]([O-])=O YWANGSCDWBUSBK-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LCRYWHVAQSCUHN-UHFFFAOYSA-N 4-amino-2-chloro-5-nitrobenzenesulfonamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1[N+]([O-])=O LCRYWHVAQSCUHN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- SEDZBBJNRJOYHT-UHFFFAOYSA-N Cl.ClC1=C(S(N)(=O)=O)C=C2NC(NC(=N)N)=NC2=C1 Chemical compound Cl.ClC1=C(S(N)(=O)=O)C=C2NC(NC(=N)N)=NC2=C1 SEDZBBJNRJOYHT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QVMFLESIHLVMFY-UHFFFAOYSA-N 2-amino-6-chloro-3H-benzimidazole-5-sulfonamide hydrobromide Chemical compound Br.ClC1=C(S(N)(=O)=O)C=C2NC(N)=NC2=C1 QVMFLESIHLVMFY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- NRZQLPCCBZGDAO-UHFFFAOYSA-N 6-chloro-2-phenyl-3h-benzimidazole-5-sulfonamide Chemical compound N=1C=2C=C(Cl)C(S(=O)(=O)N)=CC=2NC=1C1=CC=CC=C1 NRZQLPCCBZGDAO-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethanedisulfonate group Chemical class C(CS(=O)(=O)[O-])S(=O)(=O)[O-] AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89504878A | 1978-04-10 | 1978-04-10 | |
| US89504878 | 1978-04-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI791083A7 FI791083A7 (fi) | 1979-10-11 |
| FI74461B FI74461B (fi) | 1987-10-30 |
| FI74461C true FI74461C (fi) | 1988-02-08 |
Family
ID=25403870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI791083A FI74461C (fi) | 1978-04-10 | 1979-04-02 | Foerfarande foer framstaellning av bensimidazolderivat med diuretisk och antihypertensiv verkan. |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS54138561A (cs) |
| AT (1) | AT372951B (cs) |
| AU (1) | AU531086B2 (cs) |
| BE (1) | BE875425A (cs) |
| CA (1) | CA1126280A (cs) |
| DE (1) | DE2914084A1 (cs) |
| DK (1) | DK139079A (cs) |
| ES (1) | ES479446A1 (cs) |
| FI (1) | FI74461C (cs) |
| FR (1) | FR2422644A1 (cs) |
| GB (1) | GB2018766B (cs) |
| GR (1) | GR68483B (cs) |
| IL (1) | IL57105A (cs) |
| IT (1) | IT1193755B (cs) |
| NL (1) | NL7902802A (cs) |
| NZ (1) | NZ190136A (cs) |
| PT (1) | PT69458A (cs) |
| SE (1) | SE446532B (cs) |
| ZA (1) | ZA791726B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070466A (zh) * | 2010-12-28 | 2011-05-25 | 天津市筠凯化工科技有限公司 | 5-氯-2-硝基苯胺制备方法 |
| CN108558712A (zh) * | 2018-06-20 | 2018-09-21 | 新乡市锦源化工有限公司 | 一种以乙酰苯胺为原料合成高纯度对氨基苯磺酰胺的方法及对氨基苯磺酰胺 |
| CN110305018B (zh) * | 2019-06-06 | 2022-07-15 | 浙江普洛家园药业有限公司 | 一种3-溴-2-氟硝基苯的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH404675A (de) * | 1961-06-29 | 1965-12-31 | Siegfried Ag | Verfahren zur Herstellung neuer heterocyclischer Sulfonamidoverbindungen |
| FR1469504A (fr) * | 1964-10-22 | 1967-02-17 | Fisons Pest Control Ltd | Composés insecticides |
| FR1477792A (fr) * | 1965-03-24 | 1967-04-21 | Fisons Pest Control Ltd | Nouveaux benzimidazoles |
| GB1163711A (en) * | 1966-01-13 | 1969-09-10 | Fisons Pest Control Ltd | Substituted Benzimidazoles and Biocidally-Active Compositions |
| GB1356244A (en) * | 1970-07-29 | 1974-06-12 | Fisons Ltd | Substituted benzimidazole parasiticides |
-
1979
- 1979-03-26 CA CA324,146A patent/CA1126280A/en not_active Expired
- 1979-04-02 FI FI791083A patent/FI74461C/fi not_active IP Right Cessation
- 1979-04-02 SE SE7902911A patent/SE446532B/sv not_active IP Right Cessation
- 1979-04-02 AU AU45675/79A patent/AU531086B2/en not_active Ceased
- 1979-04-03 GR GR58771A patent/GR68483B/el unknown
- 1979-04-04 DK DK139079A patent/DK139079A/da not_active IP Right Cessation
- 1979-04-06 GB GB7912255A patent/GB2018766B/en not_active Expired
- 1979-04-07 DE DE19792914084 patent/DE2914084A1/de not_active Withdrawn
- 1979-04-09 PT PT69458A patent/PT69458A/pt unknown
- 1979-04-09 JP JP4211979A patent/JPS54138561A/ja active Granted
- 1979-04-09 ES ES479446A patent/ES479446A1/es not_active Expired
- 1979-04-09 BE BE0/194480A patent/BE875425A/xx not_active IP Right Cessation
- 1979-04-09 NZ NZ190136A patent/NZ190136A/xx unknown
- 1979-04-09 AT AT0263379A patent/AT372951B/de not_active IP Right Cessation
- 1979-04-09 FR FR7908945A patent/FR2422644A1/fr active Granted
- 1979-04-10 NL NL7902802A patent/NL7902802A/xx not_active Application Discontinuation
- 1979-04-10 IT IT48686/79A patent/IT1193755B/it active
- 1979-04-10 ZA ZA791726A patent/ZA791726B/xx unknown
- 1979-04-22 IL IL57105A patent/IL57105A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1193755B (it) | 1988-08-24 |
| IL57105A (en) | 1983-10-31 |
| JPS54138561A (en) | 1979-10-27 |
| ES479446A1 (es) | 1979-08-01 |
| FI74461B (fi) | 1987-10-30 |
| FR2422644B1 (cs) | 1982-12-17 |
| GB2018766A (en) | 1979-10-24 |
| AT372951B (de) | 1983-12-12 |
| DE2914084A1 (de) | 1979-10-25 |
| PT69458A (en) | 1979-05-01 |
| NL7902802A (nl) | 1979-10-12 |
| NZ190136A (en) | 1982-11-23 |
| ATA263379A (de) | 1983-04-15 |
| GR68483B (cs) | 1982-01-04 |
| AU4567579A (en) | 1979-10-18 |
| IT7948686A0 (it) | 1979-04-10 |
| CA1126280A (en) | 1982-06-22 |
| SE446532B (sv) | 1986-09-22 |
| IL57105A0 (en) | 1979-07-25 |
| BE875425A (fr) | 1979-07-31 |
| GB2018766B (en) | 1982-09-22 |
| SE7902911L (sv) | 1979-10-11 |
| AU531086B2 (en) | 1983-08-11 |
| DK139079A (da) | 1979-10-11 |
| FR2422644A1 (fr) | 1979-11-09 |
| ZA791726B (en) | 1980-05-28 |
| FI791083A7 (fi) | 1979-10-11 |
| JPH0250904B2 (cs) | 1990-11-05 |
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