BG106169A - Трициклени кондензирани хетероциклени съединения,метод за получаването и използването им - Google Patents

Трициклени кондензирани хетероциклени съединения,метод за получаването и използването им Download PDF

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Publication number: BG106169A
Authority: BG; Bulgaria
Prior art keywords: group; lower alkyl; substituted; max; compound
Prior art date: 1999-06-03

Application number

BG106169A

Other languages

Bulgarian (bg)

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

2001-12-03

Publication date

2002-05-31

2001-12-03 Application filed by Nippon Suisan Kaisha, Ltd filed Critical Nippon Suisan Kaisha, Ltd

2002-05-31 Publication of BG106169A publication Critical patent/BG106169A/bg

Links

125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 40
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 214
125000000217 alkyl group Chemical group 0.000 claims abstract description 170
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 117
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 50
229910052717 sulfur Inorganic materials 0.000 claims abstract description 48
239000001257 hydrogen Substances 0.000 claims abstract description 41
125000003118 aryl group Chemical group 0.000 claims abstract description 31
229910052760 oxygen Inorganic materials 0.000 claims abstract description 28
150000003839 salts Chemical class 0.000 claims abstract description 24
229910052799 carbon Inorganic materials 0.000 claims abstract description 17
230000008595 infiltration Effects 0.000 claims abstract description 13
238000001764 infiltration Methods 0.000 claims abstract description 13
210000005090 tracheal smooth muscle Anatomy 0.000 claims abstract description 12
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
238000006243 chemical reaction Methods 0.000 claims description 93
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 63
230000015572 biosynthetic process Effects 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 42
238000002360 preparation method Methods 0.000 claims description 41
238000000034 method Methods 0.000 claims description 38
125000001424 substituent group Chemical group 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 21
125000000304 alkynyl group Chemical group 0.000 claims description 21
230000003287 optical effect Effects 0.000 claims description 18
230000002401 inhibitory effect Effects 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
210000004969 inflammatory cell Anatomy 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
125000004442 acylamino group Chemical group 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
125000004953 trihalomethyl group Chemical group 0.000 claims description 12
238000006887 Ullmann reaction Methods 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 11
229940079593 drug Drugs 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
238000005727 Friedel-Crafts reaction Methods 0.000 claims description 10
125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
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 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
238000010511 deprotection reaction Methods 0.000 claims description 8
238000006467 substitution reaction Methods 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
238000000926 separation method Methods 0.000 claims description 7
208000002200 Respiratory Hypersensitivity Diseases 0.000 claims description 6
230000002040 relaxant effect Effects 0.000 claims description 6
230000001088 anti-asthma Effects 0.000 claims description 5
239000000924 antiasthmatic agent Substances 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000006254 cycloalkyl carbonyl group Chemical group 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
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims 13
125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 abstract description 12
210000002345 respiratory system Anatomy 0.000 abstract description 11
230000005764 inhibitory process Effects 0.000 abstract description 8
230000001629 suppression Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 327
239000000243 solution Substances 0.000 description 260
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 130
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 124
-1 methylamino, ethylamino, propylamino, dimethylamino Chemical group 0.000 description 116
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 82
239000002585 base Substances 0.000 description 76
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
239000011780 sodium chloride Substances 0.000 description 68
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 62
229920006395 saturated elastomer Polymers 0.000 description 61
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
239000002904 solvent Substances 0.000 description 54
238000003786 synthesis reaction Methods 0.000 description 54
238000005481 NMR spectroscopy Methods 0.000 description 53
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
150000001732 carboxylic acid derivatives Chemical class 0.000 description 51
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 48
239000013078 crystal Substances 0.000 description 47
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 44
239000003480 eluent Substances 0.000 description 40
239000000284 extract Substances 0.000 description 40
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
238000004809 thin layer chromatography Methods 0.000 description 35
238000001035 drying Methods 0.000 description 33
239000005457 ice water Substances 0.000 description 33
239000012043 crude product Substances 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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
241000700198 Cavia Species 0.000 description 25
239000012044 organic layer Substances 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 21
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 20
208000006673 asthma Diseases 0.000 description 18
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
239000000047 product Substances 0.000 description 18
239000000126 substance Substances 0.000 description 18
MBDUKNCPOPMRJQ-UHFFFAOYSA-N 4-amino-2-chlorobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(Cl)=C1 MBDUKNCPOPMRJQ-UHFFFAOYSA-N 0.000 description 17
QAYNSPOKTRVZRC-UHFFFAOYSA-N 99-60-5 Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl QAYNSPOKTRVZRC-UHFFFAOYSA-N 0.000 description 17
238000012360 testing method Methods 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 15
150000002391 heterocyclic compounds Chemical class 0.000 description 15
229960003424 phenylacetic acid Drugs 0.000 description 15
239000003279 phenylacetic acid Substances 0.000 description 15
241000894007 species Species 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
208000026935 allergic disease Diseases 0.000 description 14
239000000427 antigen Substances 0.000 description 14
102000036639 antigens Human genes 0.000 description 14
108091007433 antigens Proteins 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
238000001816 cooling Methods 0.000 description 13
239000000725 suspension Substances 0.000 description 13
206010020751 Hypersensitivity Diseases 0.000 description 12
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
238000001914 filtration Methods 0.000 description 11
125000005842 heteroatom Chemical group 0.000 description 11
230000009610 hypersensitivity Effects 0.000 description 11
239000001301 oxygen Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
238000003756 stirring Methods 0.000 description 11
JAVZWSOFJKYSDY-UHFFFAOYSA-N 4-bromo-2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1Cl JAVZWSOFJKYSDY-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
125000003282 alkyl amino group Chemical group 0.000 description 10
230000008602 contraction Effects 0.000 description 10
125000005843 halogen group Chemical group 0.000 description 10
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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
230000000241 respiratory effect Effects 0.000 description 9
230000004044 response Effects 0.000 description 9
229960004373 acetylcholine Drugs 0.000 description 8
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
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 7
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
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229910052786 argon Inorganic materials 0.000 description 7
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 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
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000011734 sodium Substances 0.000 description 7
239000012279 sodium borohydride Substances 0.000 description 7
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150000003573 thiols Chemical class 0.000 description 7
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235000014121 butter Nutrition 0.000 description 6
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229910052802 copper Inorganic materials 0.000 description 6
239000010949 copper Substances 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
238000010438 heat treatment Methods 0.000 description 6
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208000030603 inherited susceptibility to asthma Diseases 0.000 description 4
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HAJRFJVKAQNDLT-UHFFFAOYSA-N 2-(2-bromophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1Br HAJRFJVKAQNDLT-UHFFFAOYSA-N 0.000 description 3
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
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Classifications

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- 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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- 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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- 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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- 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)

BG106169A 1999-06-03 2001-12-03 Трициклени кондензирани хетероциклени съединения,метод за получаването и използването им BG106169A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP15718199		1999-06-03
PCT/JP2000/003592 WO2000075127A1 (fr)	1999-06-03	2000-06-02	Composes heterocycliques condenses a trois cycles, procede de preparation correspondant et utilisation de tels composes

Publications (1)

Publication Number	Publication Date
BG106169A true BG106169A (bg)	2002-05-31

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ID=15643970

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG106169A BG106169A (bg)	1999-06-03	2001-12-03	Трициклени кондензирани хетероциклени съединения,метод за получаването и използването им

Country Status (22)

Country	Link
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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GB0415320D0 (en) *	2004-07-08	2004-08-11	Astrazeneca Ab	Novel compounds
DK1710241T3 (da) *	2005-04-07	2010-03-01	Organon Nv	Intermediatforbindelser til fremstilling af trans-5-chlor-2-methyl-2,3,3a,12b-tetrahydro-1h-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol
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 (fr)	2016-11-03	2018-05-11	Sunshine Lake Pharma Co., Ltd.	Formes solides d'un composé adamantyle, compositions et utilisations de celles-ci
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
WO2024140868A1 (fr) *	2022-12-30	2024-07-04	广东东阳光药业股份有限公司	Forme cristalline d'un composé tricyclique et son utilisation

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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.
JP3328673B2 (ja)	1994-09-28	2002-09-30	日本水産株式会社	抗酸化性新規三環性縮合複素環化合物
ES2160790T3 (es)	1995-02-08	2001-11-16	Novartis Ag	10-aminoalifatil-dibenzo(b,f)oxepinas de accion antineurodegenerativa.
WO1996025927A1 (fr)	1995-02-22	1996-08-29	Nippon Suisan Kaisha, Ltd.	Inhibiteur des recepteurs de l'acide glutamique et ameliorant des fonctions cerebrales
WO1997025985A1 (fr) *	1996-01-19	1997-07-24	Nippon Suisan Kaisha, Ltd.	Relaxant des muscles lisses de la trachee
AR008371A1 (es) *	1996-05-30	2000-01-19	Novartis Ag	Una sal de adicion con acido de una 10-aminoalifatil-dibenz[b,f],oxepina, su empleo; procedimiento para su elaboracion, una 10-aminoalifatil-dibenz[b,f]oxepina, una preparacion farmaceutica que contiene dicha sal o dicha oxepina y un procedimiento para el tratamiento de enfermedades neurodegenerativ
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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
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
ZA200109565B (en)	2003-04-11

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