US3862153A - Cis-6-(acylaminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a, 10b-hexahydro-benzo {8 c{9 -{8 1,6{9 {0 naphthyridine - Google Patents
Cis-6-(acylaminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a, 10b-hexahydro-benzo {8 c{9 -{8 1,6{9 {0 naphthyridine Download PDFInfo
- Publication number
- US3862153A US3862153A US407418A US40741873A US3862153A US 3862153 A US3862153 A US 3862153A US 407418 A US407418 A US 407418A US 40741873 A US40741873 A US 40741873A US 3862153 A US3862153 A US 3862153A
- Authority
- US
- United States
- Prior art keywords
- naphthyridine
- dimethoxy
- cis
- methyl
- hexahydro
- 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.)
- Expired - Lifetime
Links
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 title description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 11
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 abstract description 4
- 239000000106 platelet aggregation inhibitor Substances 0.000 abstract description 3
- BJVCSICIEDHBNI-UHFFFAOYSA-N benzo[b][1,8]naphthyridine Chemical class N1=CC=CC2=CC3=CC=CC=C3N=C21 BJVCSICIEDHBNI-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 9
- 150000003839 salts Chemical group 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 carboxylic acid halides Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000008024 pharmaceutical diluent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 1
- 241000220479 Acacia Species 0.000 description 1
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011282 treatment Methods 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Definitions
- ABSTRACT The present invention relates to benzonaphthyridinc derivatives of the formula
- NIT-COR wherein R is dichloromethyl, cycloalkyl of 3 to 6 carbon atoms, or alkenyl of 2 to 5 carbon atoms, useful as blood platelet aggregation inhibitors.
- Nif-COR wherein R is dichloromethyl, cycloalkyl of 3 to 6 carbon atoms or alkenyl of 2 to carbon atoms.
- radical R is cycloalkyl of 3 to 6 carbon atoms, this especially contains 5 or 6 carbon atoms and may, for example, signify cyclohexyl.
- R is alkenyl of2 to 5 carbon atoms
- this radical especially signifies vinyl, or vinyl wherein l to 3 hydrogen atoms are substituted by methyl groups.
- the radical R-CONH- is preferably in the 4 position of the phenyl radical to which it is bound.
- a compound of formula I may be obtained by a process comprising acylating compounds of formula ll.
- the compounds of formula H are known or may be produced in accordance with known processes or in a manner analogous to known processes.
- Acid addition salt forms of compounds of formula I may be produced from the free base forms in conventional manner and vice versa.
- Suitable acids for acid addition salt formation include inorganic acids such as hydrochloric acid, hydrobromic acid, sulphuric acid and organic acids such as tartaric acid, benzenesulphonic acid and acetic acid.
- the reaction mixture is made alkaline with potassium carbonate and extracted with methylene chloride.
- the solution is concentrated by evaporation and the crude product is dissolved in ethanol, hydrochloric acid in ethanol is added to the solution and this is evaporated to dryness in a vacuum.
- the compounds of formula I are useful because they possess pharmacological activity in animals.
- the compounds of formula I are useful as blood platelet aggregation inhibitor agents for example in the treatment and prophylaxis of thrombosis and for improving micro-circulation in animals, as indicated by an inhibition of blood platelet aggregation induced in vitro by adenosine diphosphate in rabbit platelet-rich plasma in accordance with the turbidimetric method of Born at a concentration of from about 20 to about 30 peg/ml of the compounds.
- the dosage will, of course, vary depending on the compound employed, mode of administration and therapy desired. However, in general, satisfactory results are obtained when administered at a daily dosage of from 0.1 mg to about mg per kg animal body weight, conveniently given in divided doses two to four times a day or in sustained release form.
- the total daily dosage is in the range from about l0 to about 400mg, and dosage forms suitable for oral administration comprise from about 2 mg to about 200 mg of the compounds admixed with a solid or liquid pharmaceutical carrier or diluent.
- the compounds of formula I may be administered in pharmaceutically acceptable acid addition salt form.
- Such acid addition salt forms exhibit the same order of activity as the free base forms and readily prepared in conventional manner.
- Representative acids for addition salt formation include organic acids such as maleic, fumaric and tartaric acids and mineral acids such as hydrochloric, hydrobromic anad sulphuric acids.
- a pharmaceutical composition may comprise a compound of formula I, in free base form or in pharmaceutically acceptable acid addition salt form, in association with a pharmaceutical carrier or diluent.
- compositions conveniently contain more than 1% by weight of the compound of formula l and may be prepared by conventional techniques to be in conventional forms, for example, capsules, tablets, suppositories, dispersible powders, syrups, elixirs, suspensions or solutions,
- compositions in tablet form may be coated by Elf-COR wherein R is dichloromethyl, cycloalkyl of 3 to 6 carbon atoms or alkenyl of 2 to 5 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
- the compound of claim I which is Cis-6-( 4-acryloylaminophenyl )-8,9-dimethoxy2- methyl- 1 ,2,3,4,4a, 1 0b -hexahydro-benzo[c][ l ,6- lnaphthyridine.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1567572A CH571517A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-26 | 1972-10-26 | |
| US407418A US3862153A (en) | 1972-10-26 | 1973-10-18 | Cis-6-(acylaminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a, 10b-hexahydro-benzo {8 c{9 -{8 1,6{9 {0 naphthyridine |
| US408053A US3899494A (en) | 1970-05-13 | 1973-10-19 | Substituted 6-phenyl benzo-naphthyridines |
| NL7314396A NL7314396A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-26 | 1973-10-19 | |
| DE19732352909 DE2352909A1 (de) | 1972-10-26 | 1973-10-22 | Verfahren zur herstellung neuer heterocyclischer verbindungen |
| DD174266*A DD107457A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-26 | 1973-10-24 | |
| AU61775/73A AU6177573A (en) | 1972-10-26 | 1973-10-24 | Organic compounds |
| JP48119082A JPS4976900A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-26 | 1973-10-24 | |
| BE137082A BE806532A (fr) | 1972-10-26 | 1973-10-25 | Nouveaux derives de la naphtyridine, leur preparation et leur application comme medicaments |
| FR7338197A FR2204418A1 (en) | 1972-10-26 | 1973-10-26 | 8,9-Dimethoxy-6-acylaminophenyl-2-methyl benzo(c) (1,6)-naphthyridines - used to inhibit aggregation of blood platelets |
| US05/575,523 US3966938A (en) | 1972-10-26 | 1975-05-08 | Treatment of thrombosis and the inhibition of blood platelet aggregation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1567572A CH571517A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-26 | 1972-10-26 | |
| US407418A US3862153A (en) | 1972-10-26 | 1973-10-18 | Cis-6-(acylaminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a, 10b-hexahydro-benzo {8 c{9 -{8 1,6{9 {0 naphthyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3862153A true US3862153A (en) | 1975-01-21 |
Family
ID=25716838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US407418A Expired - Lifetime US3862153A (en) | 1970-05-13 | 1973-10-18 | Cis-6-(acylaminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a, 10b-hexahydro-benzo {8 c{9 -{8 1,6{9 {0 naphthyridine |
Country Status (3)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087530A (en) * | 1974-02-05 | 1978-05-02 | Sandoz Ltd. | Substituted 6-phenyl-octahydrobenzo [c] [1,6] naphthyridines |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3420818A (en) * | 1964-08-07 | 1969-01-07 | Sandoz Ag | Tetrahydroisoquinolines |
| US3682926A (en) * | 1971-04-19 | 1972-08-08 | Archer Sydney | Tetrahydroiso quinolinecarboxamides |
-
1972
- 1972-10-26 CH CH1567572A patent/CH571517A5/de not_active IP Right Cessation
-
1973
- 1973-10-18 US US407418A patent/US3862153A/en not_active Expired - Lifetime
- 1973-10-25 BE BE137082A patent/BE806532A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3420818A (en) * | 1964-08-07 | 1969-01-07 | Sandoz Ag | Tetrahydroisoquinolines |
| US3682926A (en) * | 1971-04-19 | 1972-08-08 | Archer Sydney | Tetrahydroiso quinolinecarboxamides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087530A (en) * | 1974-02-05 | 1978-05-02 | Sandoz Ltd. | Substituted 6-phenyl-octahydrobenzo [c] [1,6] naphthyridines |
Also Published As
| Publication number | Publication date |
|---|---|
| CH571517A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-01-15 |
| BE806532A (fr) | 1974-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5051412A (en) | Pharmaceutically active 3-(1,2,5,6-tetrahydropyridyl)-pyrrolopyridines | |
| EP0323171B1 (en) | Novel K-252 derivatives having anti-tumor activity and pharmaceutical compositions containing them | |
| EP0784622B1 (en) | Naphthyridinone derivatives | |
| JP2978850B2 (ja) | ２−アミノベンズアゼピン誘導体 | |
| CA1195324A (en) | Morphinane derivatives | |
| EP0018104B1 (en) | Tetrahydroisoquinolines, their production and the compounds and pharmaceutical compositions containing them for use in the prevention or treatment of hypertension | |
| JPH03503889A (ja) | ＰＡＦ拮抗剤としての１Ｈ／３Ｈ‐［４‐（Ｎ，Ｎ‐ジシクロアルキル／分枝アルキルカルボキサミド）‐ベンジル］イミダゾ［４，５‐ｃ］ピリジン類 | |
| EP0871447A1 (en) | Water soluble camptothecin analogs | |
| IE44379B1 (en) | Thiazolo (3,4-b)isoquinoline derivatives | |
| US4025630A (en) | Anesthesia methods using benzopyrans and esters thereof as pre-anesthesia medication | |
| US5116837A (en) | 2,9-dihydro-(6 or 7)-(3-oxo-2,3,4,5-tetrahydropyridazinyl)-pyrazolo [4,3-B]-1,4-benzoxazines | |
| US3862153A (en) | Cis-6-(acylaminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a, 10b-hexahydro-benzo {8 c{9 -{8 1,6{9 {0 naphthyridine | |
| EP0094175B1 (en) | Pyrazolopyridine compounds | |
| US4239887A (en) | Pyridothienotriazines | |
| US3860615A (en) | Tricyclic compounds and processes | |
| US3228944A (en) | Lumiergoline derivatives | |
| AU2002224086B8 (en) | Indole derivatives and use thereof in medicines | |
| JP2002516328A (ja) | Ｇ−ｃｓｆ模倣物 | |
| JP2002516329A (ja) | Ｇ−ｃｓｆ模倣物 | |
| EP0784623B1 (en) | Naphthyridine derivatives | |
| US5093339A (en) | Pyrano[f]quinoline derivatives and pharmaceutical compositions containing the same | |
| EP0653426B1 (en) | Indole derivatives, salts thereof and heart affection therapeutic agent comprising the same | |
| US4511569A (en) | Tricyclic lactams and derivatives useful in increasing cardiac contractility | |
| US3763172A (en) | Alkoxy derivatives of pyrazolopyridine carboxylic acids and esters | |
| EP0465191B1 (en) | Bicyclic sulfur-containing compounds |