ZA200109565B - Tricyclic fused heterocycle compounds, process for preparing the same and use thereof. - Google Patents
Tricyclic fused heterocycle compounds, process for preparing the same and use thereof. Download PDFInfo
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- ZA200109565B ZA200109565B ZA200109565A ZA200109565A ZA200109565B ZA 200109565 B ZA200109565 B ZA 200109565B ZA 200109565 A ZA200109565 A ZA 200109565A ZA 200109565 A ZA200109565 A ZA 200109565A ZA 200109565 B ZA200109565 B ZA 200109565B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- lower alkyl
- substituted
- alkyl group
- compound
- Prior art date
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- 125000000623 heterocyclic group Chemical group 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 225
- 125000000217 alkyl group Chemical group 0.000 claims description 162
- 238000006243 chemical reaction Methods 0.000 claims description 127
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 208000026935 allergic disease Diseases 0.000 claims description 21
- 230000003287 optical effect Effects 0.000 claims description 21
- 206010020751 Hypersensitivity Diseases 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 230000009610 hypersensitivity Effects 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 210000004969 inflammatory cell Anatomy 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000004442 acylamino group Chemical group 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 229910052721 tungsten Inorganic materials 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 230000008595 infiltration Effects 0.000 claims description 12
- 238000001764 infiltration Methods 0.000 claims description 12
- 238000006887 Ullmann reaction Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 210000005090 tracheal smooth muscle Anatomy 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 230000002040 relaxant effect Effects 0.000 claims description 8
- 239000000924 antiasthmatic agent Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- OSKIPKXMQBJWLN-UHFFFAOYSA-N 7,9-dihydroxy-3-methylsulfanyl-5h-benzo[b][1]benzothiepin-6-one Chemical compound O=C1CC2=CC(SC)=CC=C2SC2=CC(O)=CC(O)=C21 OSKIPKXMQBJWLN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 230000001088 anti-asthma Effects 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 445
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 241
- 239000000243 solution Substances 0.000 description 216
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 117
- -1 amino, carboxyl Chemical group 0.000 description 104
- 239000002904 solvent Substances 0.000 description 99
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- 239000007864 aqueous solution Substances 0.000 description 74
- 230000002829 reductive effect Effects 0.000 description 65
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 63
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 51
- 238000001035 drying Methods 0.000 description 40
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 37
- 238000004809 thin layer chromatography Methods 0.000 description 36
- 241000700198 Cavia Species 0.000 description 33
- 239000012043 crude product Substances 0.000 description 32
- 239000005457 ice water Substances 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
- 238000010898 silica gel chromatography Methods 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 208000006673 asthma Diseases 0.000 description 27
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000126 substance Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 20
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 18
- 230000005764 inhibitory process Effects 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- JAVZWSOFJKYSDY-UHFFFAOYSA-N 4-bromo-2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1Cl JAVZWSOFJKYSDY-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 230000009471 action Effects 0.000 description 14
- 125000003282 alkyl amino group Chemical group 0.000 description 14
- 239000000427 antigen Substances 0.000 description 14
- 108091007433 antigens Proteins 0.000 description 14
- 102000036639 antigens Human genes 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 150000002391 heterocyclic compounds Chemical class 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 230000004044 response Effects 0.000 description 14
- QAYNSPOKTRVZRC-UHFFFAOYSA-N 99-60-5 Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl QAYNSPOKTRVZRC-UHFFFAOYSA-N 0.000 description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 12
- 229960004373 acetylcholine Drugs 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 230000008602 contraction Effects 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 230000000144 pharmacologic effect Effects 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 10
- 239000002504 physiological saline solution Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 150000003573 thiols Chemical class 0.000 description 10
- AGXICOQOLMPJIL-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)disulfanyl]-3,5-dimethoxybenzene Chemical compound COC1=CC(OC)=CC(SSC=2C=C(OC)C=C(OC)C=2)=C1 AGXICOQOLMPJIL-UHFFFAOYSA-N 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 229960003424 phenylacetic acid Drugs 0.000 description 9
- 239000003279 phenylacetic acid Substances 0.000 description 9
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 8
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 8
- 102100032859 Protein AMBP Human genes 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 8
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- 238000010511 deprotection reaction Methods 0.000 description 7
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 7
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- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 6
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 6
- 210000003979 eosinophil Anatomy 0.000 description 6
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
- A61K31/305—Mercury compounds
- A61K31/31—Mercury compounds containing nitrogen
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A—HUMAN NECESSITIES
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- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
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- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/14—[b,f]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/14—[b,f]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15718199 | 1999-06-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200109565B true ZA200109565B (en) | 2003-04-11 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ZA200109565A ZA200109565B (en) | 1999-06-03 | 2001-11-20 | Tricyclic fused heterocycle compounds, process for preparing the same and use thereof. |
Country Status (22)
Country | Link |
---|---|
US (3) | US6602898B1 (ru) |
EP (1) | EP1182200B1 (ru) |
JP (1) | JP3471778B2 (ru) |
KR (1) | KR20020016812A (ru) |
CN (1) | CN1192027C (ru) |
AT (1) | ATE303376T1 (ru) |
AU (1) | AU777414B2 (ru) |
BG (1) | BG106169A (ru) |
BR (1) | BR0011529A (ru) |
CA (1) | CA2370013A1 (ru) |
CZ (1) | CZ20014261A3 (ru) |
DE (1) | DE60022341T2 (ru) |
DK (1) | DK1182200T3 (ru) |
ES (1) | ES2248080T3 (ru) |
HU (1) | HUP0201203A3 (ru) |
IL (1) | IL146732A0 (ru) |
NO (1) | NO20015832L (ru) |
NZ (1) | NZ515666A (ru) |
PL (1) | PL352840A1 (ru) |
RU (1) | RU2211837C2 (ru) |
WO (1) | WO2000075127A1 (ru) |
ZA (1) | ZA200109565B (ru) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0415320D0 (en) * | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
JP5773585B2 (ja) * | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
TWI698430B (zh) * | 2015-02-13 | 2020-07-11 | 南北兄弟藥業投資有限公司 | 三環化合物及其在藥物中的應用 |
TW201808283A (zh) | 2016-08-05 | 2018-03-16 | 廣東東陽光藥業有限公司 | 含氮三環化合物及其在藥物中的應用 |
WO2018082596A1 (en) | 2016-11-03 | 2018-05-11 | Sunshine Lake Pharma Co., Ltd. | Solid forms of an adamantyl compound, compositions and uses thereof |
CN110128432B (zh) * | 2018-02-02 | 2021-03-02 | 广东东阳光药业有限公司 | 含氮三环化合物及其在药物中的应用 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1302590B (ru) | 1966-08-03 | 1970-11-12 | ||
US4104280A (en) | 1977-02-04 | 1978-08-01 | Syntex (U.S.A.) Inc. | Dibenzo [b.f]thiepin and dibenzo[b.f]oxepin derivatives |
PT68303A (en) | 1977-07-26 | 1978-08-01 | Merck & Co Inc | Process for the preparation of dibenzo/b,f/thiepin |
JPS54122284A (en) | 1978-02-17 | 1979-09-21 | Dainippon Pharmaceut Co Ltd | Dibenzb,foxepin derivative |
JPS54115388A (en) | 1978-03-01 | 1979-09-07 | Nippon Chemiphar Co Ltd | Acetic acid derivative and its preparation |
US4237160A (en) | 1979-11-27 | 1980-12-02 | Merck Sharp & Dohme (I.A.) Corp. | 3-Hydroxymethyldibenzo[b,f]thiepins as prostaglandin antagonists |
DE3203065A1 (de) | 1982-01-30 | 1983-08-04 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von dibenzoxepinonen |
FR2693655B1 (fr) | 1992-07-20 | 1994-10-14 | Virbac | Vaccin antirabique avirulent. |
ATE214386T1 (de) | 1994-09-28 | 2002-03-15 | Nippon Suisan Kaisha Ltd | Neue tricyclische kondensierte heterocyclische verbindungen als antioxidantien |
EP0726265B1 (de) | 1995-02-08 | 2001-07-25 | Novartis AG | Antineurodegenerativ wirksame 10-Aminoaliphatyl-dibenz- b,f oxepine |
WO1996025927A1 (fr) | 1995-02-22 | 1996-08-29 | Nippon Suisan Kaisha, Ltd. | Inhibiteur des recepteurs de l'acide glutamique et ameliorant des fonctions cerebrales |
US6180659B1 (en) | 1996-01-19 | 2001-01-30 | Nippon Suisan Kaisha, Ltd. | Tracheal smooth muscle relaxant |
JPH10204079A (ja) * | 1997-01-20 | 1998-08-04 | Nippon Suisan Kaisha Ltd | ジベンゾオキセピンおよびジベンゾチエピン誘導体の製造方法 |
JP3283267B2 (ja) * | 1997-04-15 | 2002-05-20 | 協和醗酵工業株式会社 | 三環式化合物 |
-
2000
- 2000-06-02 AU AU51044/00A patent/AU777414B2/en not_active Ceased
- 2000-06-02 DK DK00935528T patent/DK1182200T3/da active
- 2000-06-02 KR KR1020017015458A patent/KR20020016812A/ko not_active Application Discontinuation
- 2000-06-02 PL PL00352840A patent/PL352840A1/xx not_active Application Discontinuation
- 2000-06-02 US US09/980,581 patent/US6602898B1/en not_active Expired - Fee Related
- 2000-06-02 HU HU0201203A patent/HUP0201203A3/hu unknown
- 2000-06-02 EP EP00935528A patent/EP1182200B1/en not_active Expired - Lifetime
- 2000-06-02 BR BR0011529-0A patent/BR0011529A/pt not_active IP Right Cessation
- 2000-06-02 CN CNB008084319A patent/CN1192027C/zh not_active Expired - Fee Related
- 2000-06-02 CZ CZ20014261A patent/CZ20014261A3/cs unknown
- 2000-06-02 WO PCT/JP2000/003592 patent/WO2000075127A1/ja not_active Application Discontinuation
- 2000-06-02 IL IL14673200A patent/IL146732A0/xx unknown
- 2000-06-02 NZ NZ515666A patent/NZ515666A/en unknown
- 2000-06-02 ES ES00935528T patent/ES2248080T3/es not_active Expired - Lifetime
- 2000-06-02 RU RU2001132596/04A patent/RU2211837C2/ru not_active IP Right Cessation
- 2000-06-02 AT AT00935528T patent/ATE303376T1/de not_active IP Right Cessation
- 2000-06-02 JP JP2001502410A patent/JP3471778B2/ja not_active Expired - Fee Related
- 2000-06-02 CA CA002370013A patent/CA2370013A1/en not_active Abandoned
- 2000-06-02 DE DE60022341T patent/DE60022341T2/de not_active Expired - Fee Related
-
2001
- 2001-11-20 ZA ZA200109565A patent/ZA200109565B/en unknown
- 2001-11-29 NO NO20015832A patent/NO20015832L/no not_active Application Discontinuation
- 2001-12-03 BG BG106169A patent/BG106169A/bg unknown
-
2002
- 2002-11-12 US US10/291,429 patent/US6700013B2/en not_active Expired - Fee Related
-
2003
- 2003-12-05 US US10/727,644 patent/US7410997B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CZ20014261A3 (cs) | 2002-06-12 |
US20030220360A1 (en) | 2003-11-27 |
RU2211837C2 (ru) | 2003-09-10 |
US20040127713A1 (en) | 2004-07-01 |
DE60022341D1 (de) | 2005-10-06 |
EP1182200B1 (en) | 2005-08-31 |
WO2000075127A1 (fr) | 2000-12-14 |
WO2000075127A8 (fr) | 2001-03-15 |
AU777414B2 (en) | 2004-10-14 |
EP1182200A9 (en) | 2002-05-22 |
ATE303376T1 (de) | 2005-09-15 |
BG106169A (bg) | 2002-05-31 |
CN1353703A (zh) | 2002-06-12 |
KR20020016812A (ko) | 2002-03-06 |
HUP0201203A2 (en) | 2002-08-28 |
IL146732A0 (en) | 2002-07-25 |
US7410997B2 (en) | 2008-08-12 |
JP3471778B2 (ja) | 2003-12-02 |
DK1182200T3 (da) | 2005-12-27 |
NO20015832D0 (no) | 2001-11-29 |
NZ515666A (en) | 2003-10-31 |
ES2248080T3 (es) | 2006-03-16 |
CN1192027C (zh) | 2005-03-09 |
NO20015832L (no) | 2002-02-01 |
EP1182200A1 (en) | 2002-02-27 |
PL352840A1 (en) | 2003-09-08 |
DE60022341T2 (de) | 2006-06-29 |
CA2370013A1 (en) | 2000-12-14 |
US6700013B2 (en) | 2004-03-02 |
HUP0201203A3 (en) | 2004-12-28 |
US6602898B1 (en) | 2003-08-05 |
AU5104400A (en) | 2000-12-28 |
BR0011529A (pt) | 2002-12-17 |
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