CS209950B2 - Method of making the new 4- amino-6,7-dialcoxy-2-piperazinochinazoline derivatives - Google Patents
Method of making the new 4- amino-6,7-dialcoxy-2-piperazinochinazoline derivatives Download PDFInfo
- Publication number
- CS209950B2 CS209950B2 CS802656A CS265680A CS209950B2 CS 209950 B2 CS209950 B2 CS 209950B2 CS 802656 A CS802656 A CS 802656A CS 265680 A CS265680 A CS 265680A CS 209950 B2 CS209950 B2 CS 209950B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amino
- derivatives
- formula
- compounds
- defined above
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- -1 succinimido ester Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims 1
- UDETZZKGDGINOX-UHFFFAOYSA-N [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(3,4-dihydro-2h-chromen-2-yl)methanone Chemical compound C1CC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 UDETZZKGDGINOX-UHFFFAOYSA-N 0.000 abstract description 3
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 150000003246 quinazolines Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- APKHJGDGWQDBGM-UHFFFAOYSA-N 6,7-dimethoxy-2-piperazin-1-ylquinazolin-4-amine Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCNCC1 APKHJGDGWQDBGM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- TTXLXDJZJJGALT-UHFFFAOYSA-N 3,4-dihydro-1h-isochromene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)OCCC2=C1 TTXLXDJZJJGALT-UHFFFAOYSA-N 0.000 description 1
- UXOHRZNOVPCNMD-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-2-carbonyl chloride Chemical compound C1=CC=C2OC(C(=O)Cl)CCC2=C1 UXOHRZNOVPCNMD-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WIBOFSQLDMVVLF-UHFFFAOYSA-N O.Cl.N1=CN=CC2=CC=CC=C12.N1CCNCC1 Chemical compound O.Cl.N1=CN=CC2=CC=CC=C12.N1CCNCC1 WIBOFSQLDMVVLF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7914431 | 1979-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209950B2 true CS209950B2 (en) | 1981-12-31 |
Family
ID=10504770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS802656A CS209950B2 (en) | 1979-04-25 | 1980-04-16 | Method of making the new 4- amino-6,7-dialcoxy-2-piperazinochinazoline derivatives |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4279910A (pt) |
| JP (1) | JPS55145684A (pt) |
| KR (1) | KR830002567B1 (pt) |
| AR (1) | AR224400A1 (pt) |
| AT (1) | AT373596B (pt) |
| BE (1) | BE882967A (pt) |
| CA (1) | CA1132558A (pt) |
| CH (1) | CH642076A5 (pt) |
| CS (1) | CS209950B2 (pt) |
| DD (1) | DD150202A5 (pt) |
| DE (1) | DE3015676A1 (pt) |
| DK (1) | DK121080A (pt) |
| EG (1) | EG14651A (pt) |
| ES (1) | ES8101588A1 (pt) |
| FI (1) | FI64592C (pt) |
| FR (1) | FR2455042A1 (pt) |
| GB (1) | GB2049683B (pt) |
| GR (1) | GR68049B (pt) |
| HU (1) | HU184747B (pt) |
| IE (1) | IE49705B1 (pt) |
| IL (1) | IL59900A (pt) |
| IT (1) | IT1141490B (pt) |
| LU (1) | LU82394A1 (pt) |
| NL (1) | NL182563C (pt) |
| NO (1) | NO152508C (pt) |
| NZ (1) | NZ193511A (pt) |
| PH (1) | PH15156A (pt) |
| PL (1) | PL121470B1 (pt) |
| PT (1) | PT71139A (pt) |
| SE (1) | SE435061B (pt) |
| SU (1) | SU915804A3 (pt) |
| YU (1) | YU41709B (pt) |
| ZA (1) | ZA802488B (pt) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3511836A (en) * | 1967-12-13 | 1970-05-12 | Pfizer & Co C | 2,4,6,7-tetra substituted quinazolines |
| US3663706A (en) * | 1969-09-29 | 1972-05-16 | Pfizer | Use of 2,4-diaminoquinazolines as hypotensive agents |
| US4026894A (en) * | 1975-10-14 | 1977-05-31 | Abbott Laboratories | Antihypertensive agents |
| US4001237A (en) * | 1976-02-18 | 1977-01-04 | Bristol-Myers Company | Oxazole, isoxazole, thiazole and isothiazole amides |
| US4140776A (en) * | 1977-09-16 | 1979-02-20 | Merck & Co., Inc. | N-pyrazinecarbonyl-N'-acylguanidines |
| GB2007656B (en) * | 1977-11-05 | 1982-05-19 | Pfizer Ltd | Therapeutic agents |
-
1980
- 1980-03-20 DK DK121080A patent/DK121080A/da not_active IP Right Cessation
- 1980-04-15 US US06/140,534 patent/US4279910A/en not_active Expired - Lifetime
- 1980-04-16 CS CS802656A patent/CS209950B2/cs unknown
- 1980-04-19 GR GR61722A patent/GR68049B/el unknown
- 1980-04-22 EG EG80247A patent/EG14651A/xx active
- 1980-04-23 AR AR280773A patent/AR224400A1/es active
- 1980-04-23 IT IT21598/80A patent/IT1141490B/it active
- 1980-04-23 LU LU82394A patent/LU82394A1/fr unknown
- 1980-04-23 AT AT0218980A patent/AT373596B/de not_active IP Right Cessation
- 1980-04-23 DE DE19803015676 patent/DE3015676A1/de not_active Ceased
- 1980-04-23 IL IL59900A patent/IL59900A/xx unknown
- 1980-04-23 FI FI801306A patent/FI64592C/fi not_active IP Right Cessation
- 1980-04-23 NZ NZ193511A patent/NZ193511A/xx unknown
- 1980-04-24 PH PH23945A patent/PH15156A/en unknown
- 1980-04-24 GB GB8013543A patent/GB2049683B/en not_active Expired
- 1980-04-24 SE SE8003122A patent/SE435061B/sv not_active IP Right Cessation
- 1980-04-24 YU YU1131/80A patent/YU41709B/xx unknown
- 1980-04-24 CA CA350,598A patent/CA1132558A/en not_active Expired
- 1980-04-24 IE IE827/80A patent/IE49705B1/en unknown
- 1980-04-24 SU SU802912149A patent/SU915804A3/ru active
- 1980-04-24 ES ES490867A patent/ES8101588A1/es not_active Expired
- 1980-04-24 NL NLAANVRAGE8002387,A patent/NL182563C/xx not_active IP Right Cessation
- 1980-04-24 BE BE0/200366A patent/BE882967A/fr not_active IP Right Cessation
- 1980-04-24 PT PT71139A patent/PT71139A/pt unknown
- 1980-04-24 DD DD80220686A patent/DD150202A5/de unknown
- 1980-04-24 HU HU801016A patent/HU184747B/hu unknown
- 1980-04-24 FR FR8009235A patent/FR2455042A1/fr active Granted
- 1980-04-24 JP JP5485980A patent/JPS55145684A/ja active Granted
- 1980-04-24 CH CH317280A patent/CH642076A5/de not_active IP Right Cessation
- 1980-04-24 ZA ZA00802488A patent/ZA802488B/xx unknown
- 1980-04-24 NO NO801196A patent/NO152508C/no unknown
- 1980-04-25 KR KR1019800001676A patent/KR830002567B1/ko active
- 1980-04-25 PL PL1980223755A patent/PL121470B1/pl unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0100200B1 (en) | 2-substituted 4-amino-6,7-dimethoxyquinolines | |
| EP0288973B1 (en) | Benzothiazolinone derivatives, their production and pharmaceutical composition | |
| CA2325587A1 (en) | Imidazolone anorectic agents: ii. phenyl derivatives | |
| IE56520B1 (en) | Disubstituted proline derivatives,a process for their preparation and their use | |
| US4243666A (en) | 4-Amino-2-piperidino-quinazolines | |
| JPH02124884A (ja) | Ｎ―置換アミド誘導体 | |
| CA2141366A1 (en) | Treatment of heart rhythm disorders by administration of 3-phenylsulfonyl-3,7-diazabicyclo[3.3.1]nonane compounds | |
| US4758559A (en) | Pyrrolo[1,2-a] [4,1]benzoxazepine derivatives useful as calmodulin and histamine inhibitors | |
| JPS62187452A (ja) | 環状アミン誘導体 | |
| GB2171997A (en) | 4-Amino-6,7-dimethoxy-2-Piperazin-1-ylquinazoline derivatives | |
| CS209950B2 (en) | Method of making the new 4- amino-6,7-dialcoxy-2-piperazinochinazoline derivatives | |
| JPH0228152A (ja) | コレシストキニン拮抗薬 | |
| SK281980B6 (sk) | Kryštallický (+)l-hydrogenvínan, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a jeho použitie | |
| SK13762003A3 (sk) | Deriváty 5-tio-beta-D-xylopyranozidov, spôsob ich prípravy, farmaceutické kompozície tieto deriváty obsahujúce a ich terapeutické použitie | |
| JP3748935B2 (ja) | オキシインドール誘導体 | |
| US4112102A (en) | Halopyridyl derivatives of m-aminotetramisole as anthelmintics | |
| JPH0211592A (ja) | 光学活性なジヒドロピリジンホスホン酸エステル | |
| KR820001847B1 (ko) | 4-아미노-2-피페리디노퀴나졸린 유도체의 제조방법 | |
| US4591597A (en) | Antidiabetic iminosulphonamides | |
| JP2837318B2 (ja) | アンジオテンシンｉｉ拮抗性ピリジン誘導体 | |
| US4230706A (en) | Antihypertensive quinazoline compounds | |
| CS228942B2 (en) | Method of preparing new 1-furyl-3,4-dihydroisoquinolines | |
| JPH0820586A (ja) | １−アザビシクロ［３．３．０］オクタン誘導体、その塩及び製法並びに用途 | |
| EP0342577A2 (en) | Use of dihydropyridine derivatives for the prophylaxis or treatment of cerebral circulation disorders | |
| JP3059572B2 (ja) | ピロロ［３，２−ｅ］ピラゾロ［１，５−ａ］ピリミジン誘導体及びこれを有効成分とする高血圧治療剤 |