JP2006518376A - アダマンタン誘導体、その製造方法、それらを含む医薬組成物 - Google Patents
アダマンタン誘導体、その製造方法、それらを含む医薬組成物 Download PDFInfo
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- JP2006518376A JP2006518376A JP2006502807A JP2006502807A JP2006518376A JP 2006518376 A JP2006518376 A JP 2006518376A JP 2006502807 A JP2006502807 A JP 2006502807A JP 2006502807 A JP2006502807 A JP 2006502807A JP 2006518376 A JP2006518376 A JP 2006518376A
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- compound
- chloro
- formula
- tricyclo
- ylmethyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
- 230000008569 process Effects 0.000 title abstract description 8
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 142
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
- -1 nitro, amino, hydroxyl Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000012453 solvate Substances 0.000 claims description 28
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 6
- 201000008482 osteoarthritis Diseases 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- QKXQJJGMENPLOK-RTBRYUOLSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2r)-3-(ethylamino)-2-hydroxypropyl]benzamide;hydrochloride Chemical compound Cl.CCNC[C@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 QKXQJJGMENPLOK-RTBRYUOLSA-N 0.000 claims description 4
- HZSHKJOKBLGTIS-PJARXTCWSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2s)-2-hydroxy-3-(methylamino)propyl]benzamide;hydrochloride Chemical compound Cl.CNC[C@@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 HZSHKJOKBLGTIS-PJARXTCWSA-N 0.000 claims description 4
- 230000000414 obstructive effect Effects 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 208000023504 respiratory system disease Diseases 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004889 1-methylethylamino group Chemical group CC(C)N* 0.000 claims description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- MBHCTTRXNNTXTL-IZQBTKKSSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2r)-2-hydroxy-3-(3-hydroxypropylamino)propyl]benzamide;hydrochloride Chemical compound Cl.OCCCNC[C@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 MBHCTTRXNNTXTL-IZQBTKKSSA-N 0.000 claims description 3
- YZEONRKYWDAGHN-IZQBTKKSSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2r)-2-hydroxy-3-(propan-2-ylamino)propyl]benzamide;hydrochloride Chemical compound Cl.CC(C)NC[C@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 YZEONRKYWDAGHN-IZQBTKKSSA-N 0.000 claims description 3
- LJTOAWRVCOXQEK-RTBRYUOLSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2r)-3-(dimethylamino)-2-hydroxypropyl]benzamide;hydrochloride Chemical compound Cl.CN(C)C[C@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 LJTOAWRVCOXQEK-RTBRYUOLSA-N 0.000 claims description 3
- QKXQJJGMENPLOK-BXWPFRFISA-N n-(1-adamantylmethyl)-2-chloro-5-[(2s)-3-(ethylamino)-2-hydroxypropyl]benzamide;hydrochloride Chemical compound Cl.CCNC[C@@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 QKXQJJGMENPLOK-BXWPFRFISA-N 0.000 claims description 3
- RWDNBRITKLAUTL-UHFFFAOYSA-N n-undecylbenzamide Chemical compound CCCCCCCCCCCNC(=O)C1=CC=CC=C1 RWDNBRITKLAUTL-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- XNANHPIYZJMJSP-GYVBGXKYSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2r)-3-(dimethylamino)-2-hydroxypropyl]benzamide Chemical compound CN(C)C[C@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 XNANHPIYZJMJSP-GYVBGXKYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- VOEVQROYOVSASA-LOXVZWDBSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2r)-2-hydroxy-3-(3-hydroxypropylamino)propyl]benzamide Chemical compound OCCCNC[C@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 VOEVQROYOVSASA-LOXVZWDBSA-N 0.000 claims 1
- ODPNASJTVKNROM-LOXVZWDBSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2r)-2-hydroxy-3-(propan-2-ylamino)propyl]benzamide Chemical compound CC(C)NC[C@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 ODPNASJTVKNROM-LOXVZWDBSA-N 0.000 claims 1
- UUWZPJUDHSMPBV-GYVBGXKYSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2r)-3-(ethylamino)-2-hydroxypropyl]benzamide Chemical compound CCNC[C@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 UUWZPJUDHSMPBV-GYVBGXKYSA-N 0.000 claims 1
- OBYIXHCAYXUAKA-XDHFQJGLSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2s)-2-hydroxy-3-(methylamino)propyl]benzamide Chemical compound CNC[C@@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 OBYIXHCAYXUAKA-XDHFQJGLSA-N 0.000 claims 1
- UUWZPJUDHSMPBV-HJGBXLFDSA-N n-(1-adamantylmethyl)-2-chloro-5-[(2s)-3-(ethylamino)-2-hydroxypropyl]benzamide Chemical compound CCNC[C@@H](O)CC1=CC=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 UUWZPJUDHSMPBV-HJGBXLFDSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 150000002500 ions Chemical class 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 239000003643 water by type Substances 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 9
- ROXKSVFCJKACHH-JRQWYPPZSA-N n-(1-adamantylmethyl)-2-chloro-5-[[(2r)-oxiran-2-yl]methyl]benzamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C(Cl)=CC=C1C[C@@H]1CO1 ROXKSVFCJKACHH-JRQWYPPZSA-N 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/605—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system
- C07C13/615—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system with an adamantane ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
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- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0300480A SE0300480D0 (sv) | 2003-02-21 | 2003-02-21 | Novel compounds |
| PCT/SE2004/000227 WO2004074224A1 (en) | 2003-02-21 | 2004-02-19 | Adamantane derivatives, processes for their preparation and pharmaceutical composition containing them |
Publications (2)
| Publication Number | Publication Date |
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| JP2006518376A true JP2006518376A (ja) | 2006-08-10 |
| JP2006518376A5 JP2006518376A5 (enExample) | 2007-03-15 |
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| JP2006502807A Withdrawn JP2006518376A (ja) | 2003-02-21 | 2004-02-19 | アダマンタン誘導体、その製造方法、それらを含む医薬組成物 |
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| US (1) | US7227038B2 (enExample) |
| EP (1) | EP1599432A1 (enExample) |
| JP (1) | JP2006518376A (enExample) |
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| BR (1) | BRPI0407734A (enExample) |
| CA (1) | CA2515434A1 (enExample) |
| CO (1) | CO5580815A2 (enExample) |
| IL (1) | IL169818A0 (enExample) |
| IS (1) | IS8024A (enExample) |
| MX (1) | MXPA05008690A (enExample) |
| NO (1) | NO20054329L (enExample) |
| PL (1) | PL378574A1 (enExample) |
| RU (1) | RU2005123802A (enExample) |
| SE (1) | SE0300480D0 (enExample) |
| WO (1) | WO2004074224A1 (enExample) |
| ZA (1) | ZA200506579B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI258462B (en) * | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
| SE0200920D0 (sv) * | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
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| WO2004105796A1 (en) * | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
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| GB0403864D0 (en) | 2004-02-20 | 2004-03-24 | Ucl Ventures | Modulator |
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| WO2006083214A1 (en) * | 2005-02-02 | 2006-08-10 | Astrazeneca Ab | Pharmaceutical composition comprising a p2x7 receptor antagonist and a hmg-coa reductase inhibitor |
| US20080207577A1 (en) * | 2005-07-11 | 2008-08-28 | Astrazeneca Ab | Combination I |
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| EA014779B1 (ru) | 2006-07-13 | 2011-02-28 | Янссен Фармацевтика Н.В. | Производные хиназолина в качестве mtki |
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| BRPI1014902A2 (pt) | 2009-04-14 | 2016-04-19 | Affectis Pharmaceuticals Ag | composto antagonista de p2x7r, sua composição e seus usos |
| MX2012013075A (es) | 2010-05-14 | 2012-12-17 | Affectis Pharmaceuticals Ag | Metodos novedosos para preparacion de antagonistas p2x7r. |
| WO2012110190A1 (en) | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163456A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| RU2014106611A (ru) | 2011-07-22 | 2015-08-27 | Актелион Фармасьютиклз Лтд | Производные гетероциклических амидов в качестве антагонистов р2х7 рецептора |
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| CA2891090A1 (en) * | 2012-11-09 | 2014-05-15 | Scidose, Llc | Enema composition for treatment of ulcerative colitis having long term stability |
| PL2931717T3 (pl) | 2012-12-12 | 2017-05-31 | Actelion Pharmaceuticals Ltd. | Pochodne indolokarboksyamidu jako antagoniści receptora p2x7 |
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| EP2956457B1 (en) | 2013-01-22 | 2016-11-23 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
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| US3464998A (en) | 1968-03-04 | 1969-09-02 | Searle & Co | Adamantyl esters and amides of pyridinecarboxylic acids |
| GB1274652A (en) | 1968-08-27 | 1972-05-17 | Lilly Industries Ltd | Adamantanyl-alkylamine derivatives and their preparation |
| IL53441A0 (en) | 1977-11-22 | 1978-01-31 | Teva Pharma | Methyladamantyl hydrazines their preparation and pharmaceutical compositions containing them |
| US4349552A (en) | 1978-10-30 | 1982-09-14 | Fujisawa Pharmaceutical Company, Ltd. | 5-Fluorouracil derivatives, and their pharmaceutical compositions |
| US4751292A (en) | 1985-07-02 | 1988-06-14 | The Plant Cell Research Institute, Inc. | Adamantyl purines |
| AU682051B2 (en) | 1993-08-10 | 1997-09-18 | James Black Foundation Limited | Gastrin and CCK receptor ligands |
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| ZA988967B (en) | 1997-10-03 | 2000-04-03 | Du Pont Pharm Co | Lactam metalloprotease inhibitors. |
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| SE9704545D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| WO2000061569A1 (en) | 1999-04-09 | 2000-10-19 | Astrazeneca Ab | Adamantane derivatives |
| SE9904505D0 (sv) | 1999-12-09 | 1999-12-09 | Astra Pharma Prod | Novel compounds |
| TWI258462B (en) * | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
| GB0013737D0 (en) | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
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| PA8557501A1 (es) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
| WO2003042190A1 (en) | 2001-11-12 | 2003-05-22 | Pfizer Products Inc. | N-alkyl-adamantyl derivatives as p2x7-receptor antagonists |
| SE0103836D0 (sv) * | 2001-11-16 | 2001-11-16 | Astrazeneca Ab | Novel compounds |
| SE0200920D0 (sv) | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
| SE0300445D0 (sv) | 2003-02-18 | 2003-02-18 | Astrazeneca Ab | New combination |
| WO2004105796A1 (en) | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
| WO2004105797A1 (en) | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
| KR20060037258A (ko) | 2003-05-29 | 2006-05-03 | 아스트라제네카 아베 | Ｐ2Ｘ7-수용체 길항제 및 종양 괴사 인자 α를 포함하는제약 조성물 |
| SE0302192D0 (sv) | 2003-08-08 | 2003-08-08 | Astrazeneca Ab | Novel compounds |
| SE0302488D0 (sv) | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | New combination |
-
2003
- 2003-02-21 SE SE0300480A patent/SE0300480D0/xx unknown
-
2004
- 2004-02-19 WO PCT/SE2004/000227 patent/WO2004074224A1/en not_active Ceased
- 2004-02-19 RU RU2005123802/04A patent/RU2005123802A/ru not_active Application Discontinuation
- 2004-02-19 AU AU2004213356A patent/AU2004213356B2/en not_active Ceased
- 2004-02-19 US US10/546,131 patent/US7227038B2/en not_active Expired - Fee Related
- 2004-02-19 BR BRPI0407734-2A patent/BRPI0407734A/pt not_active IP Right Cessation
- 2004-02-19 EP EP04712798A patent/EP1599432A1/en not_active Withdrawn
- 2004-02-19 JP JP2006502807A patent/JP2006518376A/ja not_active Withdrawn
- 2004-02-19 MX MXPA05008690A patent/MXPA05008690A/es unknown
- 2004-02-19 KR KR1020057015302A patent/KR20050101559A/ko not_active Withdrawn
- 2004-02-19 CN CNB2004800047676A patent/CN100378047C/zh not_active Expired - Fee Related
- 2004-02-19 PL PL378574A patent/PL378574A1/pl not_active Application Discontinuation
- 2004-02-19 CA CA002515434A patent/CA2515434A1/en not_active Abandoned
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2005
- 2005-07-21 IL IL169818A patent/IL169818A0/en unknown
- 2005-08-02 CO CO05076011A patent/CO5580815A2/es not_active Application Discontinuation
- 2005-08-17 ZA ZA200506579A patent/ZA200506579B/en unknown
- 2005-09-14 IS IS8024A patent/IS8024A/is unknown
- 2005-09-20 NO NO20054329A patent/NO20054329L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL378574A1 (pl) | 2006-05-02 |
| AU2004213356A1 (en) | 2004-09-02 |
| CO5580815A2 (es) | 2005-11-30 |
| IL169818A0 (en) | 2007-07-04 |
| US7227038B2 (en) | 2007-06-05 |
| CN1751010A (zh) | 2006-03-22 |
| KR20050101559A (ko) | 2005-10-24 |
| NO20054329D0 (no) | 2005-09-20 |
| NO20054329L (no) | 2005-11-21 |
| CN100378047C (zh) | 2008-04-02 |
| SE0300480D0 (sv) | 2003-02-21 |
| RU2005123802A (ru) | 2006-02-27 |
| CA2515434A1 (en) | 2004-09-02 |
| BRPI0407734A (pt) | 2006-02-14 |
| MXPA05008690A (es) | 2005-10-05 |
| IS8024A (is) | 2005-09-14 |
| EP1599432A1 (en) | 2005-11-30 |
| AU2004213356B2 (en) | 2007-03-15 |
| ZA200506579B (en) | 2006-05-31 |
| US20060160904A1 (en) | 2006-07-20 |
| WO2004074224A1 (en) | 2004-09-02 |
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