HU203234B - Process for producing new, multiply oxygenated labdane derivatives and pharmaceutical compositions comprising such compounds as active ingredient - Google Patents
Process for producing new, multiply oxygenated labdane derivatives and pharmaceutical compositions comprising such compounds as active ingredient Download PDFInfo
- Publication number
- HU203234B HU203234B HU864152A HU415286A HU203234B HU 203234 B HU203234 B HU 203234B HU 864152 A HU864152 A HU 864152A HU 415286 A HU415286 A HU 415286A HU 203234 B HU203234 B HU 203234B
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- HU
- Hungary
- Prior art keywords
- formula
- hydrogen
- group
- epoxy
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 67
- 238000000034 method Methods 0.000 title claims description 19
- 230000008569 process Effects 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000001761 labdane diterpenoid derivatives Chemical class 0.000 title abstract 2
- 239000004480 active ingredient Substances 0.000 title description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- -1 piperidino, pyrrolidino, morpholino, thiomorpholino Chemical group 0.000 claims description 118
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical group O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000493 isoindolonyl group Chemical group C1(N=C(C2=CC=CC=C12)*)=O 0.000 claims description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 abstract description 5
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
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- 125000000266 alpha-aminoacyl group Chemical group 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
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- 201000010099 disease Diseases 0.000 abstract description 2
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- 229940121354 immunomodulator Drugs 0.000 abstract description 2
- 230000000747 cardiac effect Effects 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
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- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 8
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 8
- 150000004682 monohydrates Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 6
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- DBODNPMIIRVQGW-UHFFFAOYSA-N trihydrate;dihydrochloride Chemical compound O.O.O.Cl.Cl DBODNPMIIRVQGW-UHFFFAOYSA-N 0.000 description 6
- 230000003276 anti-hypertensive effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000000297 inotrophic effect Effects 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
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- 241000700199 Cavia porcellus Species 0.000 description 3
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- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000572 bronchospasmolytic effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WPDITXOBNLYZHH-UHFFFAOYSA-N desacetylforskolin Natural products O1C(C)(C=C)CC(=O)C2(O)C3(C)C(O)CCC(C)(C)C3C(O)C(O)C21C WPDITXOBNLYZHH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 238000001727 in vivo Methods 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
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229940053973 novocaine Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 210000004417 patella Anatomy 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 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
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 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
- C07D405/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853535086 DE3535086A1 (de) | 1985-10-02 | 1985-10-02 | Neue polyoxygenierte labdan-derivate, verfahren zu ihrer herstellung und ihre anwendung als medikamente |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT46319A HUT46319A (en) | 1988-10-28 |
| HU203234B true HU203234B (en) | 1991-06-28 |
Family
ID=6282512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU864152A HU203234B (en) | 1985-10-02 | 1986-10-01 | Process for producing new, multiply oxygenated labdane derivatives and pharmaceutical compositions comprising such compounds as active ingredient |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0217372B1 (OSRAM) |
| JP (1) | JPS6289677A (OSRAM) |
| KR (1) | KR870004051A (OSRAM) |
| AT (1) | ATE60054T1 (OSRAM) |
| AU (1) | AU606036B2 (OSRAM) |
| DE (2) | DE3535086A1 (OSRAM) |
| DK (1) | DK468186A (OSRAM) |
| ES (1) | ES2019863B3 (OSRAM) |
| GR (1) | GR3001559T3 (OSRAM) |
| HU (1) | HU203234B (OSRAM) |
| IL (1) | IL80201A0 (OSRAM) |
| IN (2) | IN163242B (OSRAM) |
| PT (1) | PT83478B (OSRAM) |
| ZA (1) | ZA867495B (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963537A (en) * | 1985-03-01 | 1990-10-16 | Hoechst-Roussel Pharmaceuticals Inc. | Labdane compounds, pharmaceutical compositions and use |
| DE3678736D1 (de) * | 1985-03-01 | 1991-05-23 | Hoechst Roussel Pharma | Labdanderivate, verfahren zu deren herstellung und deren verwendung als arzneimittel. |
| JPS6310783A (ja) * | 1985-11-15 | 1988-01-18 | Nippon Kayaku Co Ltd | 新規フオルスコリン誘導体 |
| AU591196B2 (en) * | 1985-11-15 | 1989-11-30 | Nippon Kayaku Kabushiki Kaisha | Novel forskolin derivatives |
| DE3623300A1 (de) * | 1986-07-11 | 1988-01-21 | Hoechst Ag | 7-acyloxy-6-aminoacyloxypolyoxylabdane, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US5646175A (en) * | 1987-12-28 | 1997-07-08 | Hoechst Marion Roussel, Inc. | Carbamoyloxylabdane compounds |
| US4920146A (en) * | 1986-12-29 | 1990-04-24 | Hoechst Roussel Pharmaceuticals Inc. | Carbamoyloxylabdane compounds useful in reducing intraocular pressure |
| IN166900B (OSRAM) * | 1987-06-03 | 1990-08-04 | Hoechst India | |
| JPH0684367B2 (ja) * | 1987-06-29 | 1994-10-26 | 日本化薬株式会社 | フオルスコリン誘導体の新規製造法 |
| JP2504934B2 (ja) * | 1987-06-29 | 1996-06-05 | 日本化薬株式会社 | １，６，７−トリアシルフオルスコリン誘導体 |
| US5846992A (en) * | 1987-10-08 | 1998-12-08 | Hoechst Marion Roussel, Inc. | Synergistic intraocular pressure lowering combinations |
| US4902696A (en) * | 1987-10-08 | 1990-02-20 | Hoechst-Roussel Pharmaceuticals, Inc. | Synergistic intraocular pressure lowering combinations |
| US4883793A (en) * | 1988-05-09 | 1989-11-28 | Hoechst-Roussel Pharmaceuticals Inc. | Hydrazinocarbonyloxylabdanes for treating cardiac failure |
| EP0447962A1 (en) * | 1990-03-17 | 1991-09-25 | Hoechst Aktiengesellschaft | Labdanes and process for their preparation |
| YU128291A (sh) * | 1990-07-24 | 1994-09-09 | Joechst Aktiengesellschaft | Postpak za dobijanje 6-(3-substituisanih aminopropionil) 7-deacetilforskolinskih derivata |
| JP3557095B2 (ja) * | 1998-04-20 | 2004-08-25 | 高砂香料工業株式会社 | メラニン産生抑制剤 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2557784C2 (de) | 1975-12-22 | 1986-04-17 | Hoechst Ag, 6230 Frankfurt | Forskolin, Verfahren zu dessen Gewinnung und diese Verbindung enthaltende pharmazeutische Präparate |
| DE2640275A1 (de) | 1976-09-08 | 1978-03-09 | Hoechst Ag | Pharmakologisch wirksame substanz aus labiaten |
| DE2654796A1 (de) * | 1976-12-03 | 1978-06-08 | Hoechst Ag | Polyoxygenierte labdan-derivate |
| FR2460397A1 (fr) * | 1979-07-05 | 1981-01-23 | Ducellier & Cie | Demarreur electrique pour moteurs a combustion interne notamment de vehicules automobiles |
| DE3502685A1 (de) | 1985-01-26 | 1986-09-04 | Hoechst Ag, 6230 Frankfurt | Forskolin, seine analoge und derivate, verfahren zu deren herstellung mittels mikrobieller umwandlungen und die anwendung dieser verbindungen als arzneimittel |
| DE3581725D1 (de) * | 1984-12-14 | 1991-03-14 | Hoechst Roussel Pharma | Aminoacyllabdane, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als arzneimittel. |
| US4639443A (en) * | 1985-03-01 | 1987-01-27 | Hoechst-Roussel Pharmaceuticals Inc. | Labdane compounds, pharmaceutical compositions and use |
| DE3678736D1 (de) * | 1985-03-01 | 1991-05-23 | Hoechst Roussel Pharma | Labdanderivate, verfahren zu deren herstellung und deren verwendung als arzneimittel. |
| AU591196B2 (en) * | 1985-11-15 | 1989-11-30 | Nippon Kayaku Kabushiki Kaisha | Novel forskolin derivatives |
-
1985
- 1985-05-03 IN IN122/BOM/85A patent/IN163242B/en unknown
- 1985-10-02 DE DE19853535086 patent/DE3535086A1/de not_active Withdrawn
-
1986
- 1986-09-30 AU AU63270/86A patent/AU606036B2/en not_active Ceased
- 1986-09-30 IL IL80201A patent/IL80201A0/xx unknown
- 1986-10-01 EP EP86113486A patent/EP0217372B1/de not_active Expired - Lifetime
- 1986-10-01 HU HU864152A patent/HU203234B/hu not_active IP Right Cessation
- 1986-10-01 ES ES86113486T patent/ES2019863B3/es not_active Expired - Lifetime
- 1986-10-01 PT PT83478A patent/PT83478B/pt not_active IP Right Cessation
- 1986-10-01 DK DK468186A patent/DK468186A/da unknown
- 1986-10-01 DE DE8686113486T patent/DE3676922D1/de not_active Expired - Fee Related
- 1986-10-01 AT AT86113486T patent/ATE60054T1/de not_active IP Right Cessation
- 1986-10-01 JP JP61231365A patent/JPS6289677A/ja active Pending
- 1986-10-01 ZA ZA867495A patent/ZA867495B/xx unknown
- 1986-10-02 KR KR1019860008271A patent/KR870004051A/ko not_active Ceased
-
1988
- 1988-03-18 IN IN70/BOM/88A patent/IN164680B/en unknown
-
1991
- 1991-03-06 GR GR91400111T patent/GR3001559T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN163242B (OSRAM) | 1988-08-27 |
| AU606036B2 (en) | 1991-01-31 |
| DK468186D0 (da) | 1986-10-01 |
| PT83478B (pt) | 1989-05-31 |
| GR3001559T3 (en) | 1992-11-23 |
| KR870004051A (ko) | 1987-05-07 |
| ES2019863B3 (es) | 1991-07-16 |
| EP0217372B1 (de) | 1991-01-16 |
| EP0217372A2 (de) | 1987-04-08 |
| ZA867495B (en) | 1987-05-27 |
| IN164680B (OSRAM) | 1989-05-06 |
| HUT46319A (en) | 1988-10-28 |
| AU6327086A (en) | 1987-04-09 |
| DE3535086A1 (de) | 1987-04-16 |
| PT83478A (de) | 1986-11-01 |
| JPS6289677A (ja) | 1987-04-24 |
| EP0217372A3 (en) | 1988-03-30 |
| DE3676922D1 (de) | 1991-02-21 |
| IL80201A0 (en) | 1986-12-31 |
| DK468186A (da) | 1987-04-03 |
| ATE60054T1 (de) | 1991-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |