CA2598969A1 - Derives de 6, 7, 8, 9-tetrahydro-5-amino-5h-benzocycloheptene-6-ole et composes apparentes comme inhibiteurs d'inflammation - Google Patents
Derives de 6, 7, 8, 9-tetrahydro-5-amino-5h-benzocycloheptene-6-ole et composes apparentes comme inhibiteurs d'inflammation Download PDFInfo
- Publication number
- CA2598969A1 CA2598969A1 CA002598969A CA2598969A CA2598969A1 CA 2598969 A1 CA2598969 A1 CA 2598969A1 CA 002598969 A CA002598969 A CA 002598969A CA 2598969 A CA2598969 A CA 2598969A CA 2598969 A1 CA2598969 A1 CA 2598969A1
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- CA
- Canada
- Prior art keywords
- group
- groups
- alkyl
- optionally
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 title claims description 95
- 239000002260 anti-inflammatory agent Substances 0.000 title abstract description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 title abstract description 4
- BTRCHTMVMNPPSF-UHFFFAOYSA-N 5-amino-6,7,8,9-tetrahydro-5h-benzo[7]annulen-6-ol Chemical class NC1C(O)CCCC2=CC=CC=C12 BTRCHTMVMNPPSF-UHFFFAOYSA-N 0.000 title description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 94
- 125000005843 halogen group Chemical group 0.000 claims abstract description 69
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 37
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- XHVULKQHRQZNMW-UHFFFAOYSA-N 5H-benzocycloheptene Chemical class C1C=CC=CC2=CC=CC=C12 XHVULKQHRQZNMW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- -1 thiophthalidyl Chemical group 0.000 claims description 191
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 30
- HEOQXHNKRXRCTO-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulene Chemical compound C1CCCCC2=CC=CC=C21 HEOQXHNKRXRCTO-UHFFFAOYSA-N 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 150000001412 amines Chemical class 0.000 claims description 28
- 208000010668 atopic eczema Diseases 0.000 claims description 28
- 125000000468 ketone group Chemical group 0.000 claims description 26
- 230000002757 inflammatory effect Effects 0.000 claims description 25
- 230000000172 allergic effect Effects 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 230000002062 proliferating effect Effects 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000002619 bicyclic group Chemical group 0.000 claims description 17
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 16
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 14
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
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- 125000001041 indolyl group Chemical group 0.000 claims description 14
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 14
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 13
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- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000005633 phthalidyl group Chemical group 0.000 claims description 13
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
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- 125000004429 atom Chemical group 0.000 claims description 12
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- 150000002466 imines Chemical class 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 8
- 150000007517 lewis acids Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000008177 pharmaceutical agent Substances 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 208000025747 Rheumatic disease Diseases 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 238000003408 phase transfer catalysis Methods 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 208000012659 Joint disease Diseases 0.000 claims description 2
- 208000019693 Lung disease Diseases 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 230000007815 allergy Effects 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 208000030172 endocrine system disease Diseases 0.000 claims description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 2
- 208000030533 eye disease Diseases 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
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- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 5
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims 1
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims 1
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- 150000002823 nitrates Chemical class 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 125000005547 pivalate group Chemical group 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000004419 alkynylene group Chemical group 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- 239000002904 solvent Substances 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
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- 239000000243 solution Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Neurosurgery (AREA)
- Pregnancy & Childbirth (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005014090A DE102005014090A1 (de) | 2005-03-22 | 2005-03-22 | 5H-Benzocycloheptenderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer |
| DE102005014090.4 | 2005-03-22 | ||
| PCT/EP2006/002742 WO2006100099A1 (fr) | 2005-03-22 | 2006-03-20 | Derives de 6, 7, 8, 9-tetrahydro-5-amino-5h-benzocycloheptene-6-ole et composes apparentes comme inhibiteurs d'inflammation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2598969A1 true CA2598969A1 (fr) | 2006-09-28 |
Family
ID=36589218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002598969A Abandoned CA2598969A1 (fr) | 2005-03-22 | 2006-03-20 | Derives de 6, 7, 8, 9-tetrahydro-5-amino-5h-benzocycloheptene-6-ole et composes apparentes comme inhibiteurs d'inflammation |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1863765A1 (fr) |
| JP (1) | JP2008534462A (fr) |
| CN (1) | CN101146773A (fr) |
| AR (1) | AR053189A1 (fr) |
| CA (1) | CA2598969A1 (fr) |
| DE (1) | DE102005014090A1 (fr) |
| DO (1) | DOP2006000065A (fr) |
| GT (1) | GT200600124A (fr) |
| PA (1) | PA8666801A1 (fr) |
| PE (1) | PE20061350A1 (fr) |
| TW (1) | TW200700389A (fr) |
| UY (1) | UY29435A1 (fr) |
| WO (1) | WO2006100099A1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201806829TA (en) * | 2016-02-15 | 2018-09-27 | Sanofi Sa | 6,7-dihydro-5h-benzo[7]annulene derivatives as estrogen receptor modulators |
| CN107118173B (zh) * | 2017-07-12 | 2019-10-29 | 阿里生物新材料（常州）有限公司 | 一种环庚三烯并噁嗪类化合物及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU8402275A (en) * | 1974-08-26 | 1977-02-17 | Takeda Chemical Industries Ltd | Benzocycloheptene derivatives |
| NZ224622A (en) * | 1987-05-15 | 1992-06-25 | Schering Corp | Benzoxepine, benzazepine and benzocycloheptene derivatives and pharmaceutical compositions |
| PT87988B (pt) * | 1987-07-16 | 1995-05-04 | Byk Gulden Lomberg Chem Fab | Processo para a preparacao de diazois e de composicoes farmaceuticas que os contem |
| WO1999005107A1 (fr) * | 1997-07-25 | 1999-02-04 | Smithkline Beecham Corporation | Antagonistes du recepteur de vitronectine |
| JP2006516989A (ja) * | 2003-02-07 | 2006-07-13 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 抗菌剤として使用するための二環式環によりｎ−置換されたオキサゾリジノン誘導体 |
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2005
- 2005-03-22 DE DE102005014090A patent/DE102005014090A1/de not_active Withdrawn
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2006
- 2006-03-20 JP JP2008502339A patent/JP2008534462A/ja active Pending
- 2006-03-20 CA CA002598969A patent/CA2598969A1/fr not_active Abandoned
- 2006-03-20 CN CNA2006800096370A patent/CN101146773A/zh active Pending
- 2006-03-20 WO PCT/EP2006/002742 patent/WO2006100099A1/fr not_active Application Discontinuation
- 2006-03-20 EP EP06723721A patent/EP1863765A1/fr not_active Withdrawn
- 2006-03-21 DO DO2006000065A patent/DOP2006000065A/es unknown
- 2006-03-21 GT GT200600124A patent/GT200600124A/es unknown
- 2006-03-21 PE PE2006000307A patent/PE20061350A1/es not_active Application Discontinuation
- 2006-03-21 UY UY29435A patent/UY29435A1/es not_active Application Discontinuation
- 2006-03-21 PA PA20068666801A patent/PA8666801A1/es unknown
- 2006-03-22 TW TW095109925A patent/TW200700389A/zh unknown
- 2006-03-22 AR ARP060101120A patent/AR053189A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UY29435A1 (es) | 2006-10-02 |
| AR053189A1 (es) | 2007-04-25 |
| JP2008534462A (ja) | 2008-08-28 |
| GT200600124A (es) | 2007-01-03 |
| PA8666801A1 (es) | 2006-09-22 |
| EP1863765A1 (fr) | 2007-12-12 |
| CN101146773A (zh) | 2008-03-19 |
| DE102005014090A1 (de) | 2006-09-28 |
| DOP2006000065A (es) | 2006-10-15 |
| PE20061350A1 (es) | 2006-12-20 |
| TW200700389A (en) | 2007-01-01 |
| WO2006100099A1 (fr) | 2006-09-28 |
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