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 PDF

Info

Publication number: ZA200109565B
Authority: ZA; South Africa
Prior art keywords: group; lower alkyl; substituted; alkyl group; compound
Prior art date: 1999-06-03

Application number

ZA200109565A

Other languages

English (en)

Inventor

Shuji Jinno

Takaaki Okita

Naomi Ohtsuka

Shinya Yamashita

Junichiro Hata

Jiro Takeo

Original Assignee

Nippon Suisan Kaisha Ltd

Priority date (The priority date 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 date listed.)

1999-06-03

Filing date

2001-11-20

Publication date

2003-04-11

2001-11-20 Application filed by Nippon Suisan Kaisha Ltd filed Critical Nippon Suisan Kaisha Ltd

2003-04-11 Publication of ZA200109565B publication Critical patent/ZA200109565B/en

Links

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
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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
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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
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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
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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
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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
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210000000440 neutrophil Anatomy 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
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XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 description 1
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239000013641 positive control Substances 0.000 description 1
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239000000050 smooth muscle relaxant Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
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235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
OVNNRVBQIIDEDN-UHFFFAOYSA-M sodium;8-ethylsulfanyl-1,3-dimethyl-6-sulfanylidenepurin-7-id-2-one Chemical compound [Na+].CN1C(=O)N(C)C(=S)C2=C1N=C(SCC)[N-]2 OVNNRVBQIIDEDN-UHFFFAOYSA-M 0.000 description 1
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238000012453 sprague-dawley rat model Methods 0.000 description 1
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150000003431 steroids Chemical class 0.000 description 1
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235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
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NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
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238000000772 tip-enhanced Raman spectroscopy Methods 0.000 description 1
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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
- C07D405/04—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
- 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
- A61K31/28—Compounds containing heavy metals
- A61K31/305—Mercury compounds
- A61K31/31—Mercury compounds containing nitrogen
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- 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
- A61K31/335—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
- 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
- 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
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
- 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
- A61K31/4353—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
- 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
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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]
- 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)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (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)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (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)

ZA200109565A 1999-06-03 2001-11-20 Tricyclic fused heterocycle compounds, process for preparing the same and use thereof. ZA200109565B (en)

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US (3)	US6602898B1 (fr)
EP (1)	EP1182200B1 (fr)
JP (1)	JP3471778B2 (fr)
KR (1)	KR20020016812A (fr)
CN (1)	CN1192027C (fr)
AT (1)	ATE303376T1 (fr)
AU (1)	AU777414B2 (fr)
BG (1)	BG106169A (fr)
BR (1)	BR0011529A (fr)
CA (1)	CA2370013A1 (fr)
CZ (1)	CZ20014261A3 (fr)
DE (1)	DE60022341T2 (fr)
DK (1)	DK1182200T3 (fr)
ES (1)	ES2248080T3 (fr)
HU (1)	HUP0201203A3 (fr)
IL (1)	IL146732A0 (fr)
NO (1)	NO20015832L (fr)
NZ (1)	NZ515666A (fr)
PL (1)	PL352840A1 (fr)
RU (1)	RU2211837C2 (fr)
WO (1)	WO2000075127A1 (fr)
ZA (1)	ZA200109565B (fr)

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Publication number	Priority date	Publication date	Assignee	Title
GB0415320D0 (en) *	2004-07-08	2004-08-11	Astrazeneca Ab	Novel compounds
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2000
- 2000-06-02 IL IL14673200A patent/IL146732A0/xx unknown
- 2000-06-02 EP EP00935528A patent/EP1182200B1/fr not_active Expired - Lifetime
- 2000-06-02 HU HU0201203A patent/HUP0201203A3/hu unknown
- 2000-06-02 WO PCT/JP2000/003592 patent/WO2000075127A1/fr not_active Ceased
- 2000-06-02 US US09/980,581 patent/US6602898B1/en not_active Expired - Fee Related
- 2000-06-02 PL PL00352840A patent/PL352840A1/xx not_active Application Discontinuation
- 2000-06-02 CZ CZ20014261A patent/CZ20014261A3/cs unknown
- 2000-06-02 KR KR1020017015458A patent/KR20020016812A/ko not_active Ceased
- 2000-06-02 ES ES00935528T patent/ES2248080T3/es not_active Expired - Lifetime
- 2000-06-02 NZ NZ515666A patent/NZ515666A/en unknown
- 2000-06-02 AU AU51044/00A patent/AU777414B2/en not_active Ceased
- 2000-06-02 CA CA002370013A patent/CA2370013A1/fr not_active Abandoned
- 2000-06-02 DK DK00935528T patent/DK1182200T3/da active
- 2000-06-02 AT AT00935528T patent/ATE303376T1/de not_active IP Right Cessation
- 2000-06-02 RU RU2001132596/04A patent/RU2211837C2/ru not_active IP Right Cessation
- 2000-06-02 DE DE60022341T patent/DE60022341T2/de not_active Expired - Fee Related
- 2000-06-02 BR BR0011529-0A patent/BR0011529A/pt not_active IP Right Cessation
- 2000-06-02 JP JP2001502410A patent/JP3471778B2/ja not_active Expired - Fee Related
- 2000-06-02 CN CNB008084319A patent/CN1192027C/zh 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
NO20015832D0 (no)	2001-11-29
BR0011529A (pt)	2002-12-17
CA2370013A1 (fr)	2000-12-14
US6700013B2 (en)	2004-03-02
DK1182200T3 (da)	2005-12-27
CN1192027C (zh)	2005-03-09
ATE303376T1 (de)	2005-09-15
NZ515666A (en)	2003-10-31
IL146732A0 (en)	2002-07-25
US20030220360A1 (en)	2003-11-27
US20040127713A1 (en)	2004-07-01
AU5104400A (en)	2000-12-28
US7410997B2 (en)	2008-08-12
EP1182200B1 (fr)	2005-08-31
WO2000075127A8 (fr)	2001-03-15
EP1182200A9 (fr)	2002-05-22
EP1182200A1 (fr)	2002-02-27
BG106169A (bg)	2002-05-31
HUP0201203A3 (en)	2004-12-28
JP3471778B2 (ja)	2003-12-02
PL352840A1 (en)	2003-09-08
CN1353703A (zh)	2002-06-12
KR20020016812A (ko)	2002-03-06
WO2000075127A1 (fr)	2000-12-14
NO20015832L (no)	2002-02-01
DE60022341D1 (de)	2005-10-06
DE60022341T2 (de)	2006-06-29
US6602898B1 (en)	2003-08-05
HUP0201203A2 (en)	2002-08-28
RU2211837C2 (ru)	2003-09-10
AU777414B2 (en)	2004-10-14
CZ20014261A3 (cs)	2002-06-12
ES2248080T3 (es)	2006-03-16

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