RU2468028C2 - Спироциклические азаиндольные производные - Google Patents
Спироциклические азаиндольные производные Download PDFInfo
- Publication number
- RU2468028C2 RU2468028C2 RU2009105399/04A RU2009105399A RU2468028C2 RU 2468028 C2 RU2468028 C2 RU 2468028C2 RU 2009105399/04 A RU2009105399/04 A RU 2009105399/04A RU 2009105399 A RU2009105399 A RU 2009105399A RU 2468028 C2 RU2468028 C2 RU 2468028C2
- Authority
- RU
- Russia
- Prior art keywords
- spiro
- indole
- aza
- cyclohexane
- tetrahydropyrano
- Prior art date
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- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 157
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
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- 239000003814 drug Substances 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 230000036407 pain Effects 0.000 claims abstract description 17
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 7
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 277
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 257
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 100
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 89
- -1 benzodioxolanyl Chemical group 0.000 claims description 81
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 61
- 239000002904 solvent Substances 0.000 claims description 57
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- 125000000217 alkyl group Chemical group 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 21
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- 229940079593 drug Drugs 0.000 claims description 15
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- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000003444 anaesthetic effect Effects 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 4
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 4
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
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- 230000001476 alcoholic effect Effects 0.000 claims description 2
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- 238000011260 co-administration Methods 0.000 claims description 2
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- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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Classifications
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- 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
- C07D491/12—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 three hetero rings
- C07D491/14—Ortho-condensed 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
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/12—Antidiarrhoeals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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| DE102006033114.1 | 2006-07-18 | ||
| DE102006033114A DE102006033114A1 (de) | 2006-07-18 | 2006-07-18 | Spirocyclische Azaindol-Derivate |
| PCT/EP2007/006326 WO2008009416A1 (de) | 2006-07-18 | 2007-07-17 | Spirocyclische azaindol-derivate |
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| RU2009105399A RU2009105399A (ru) | 2010-08-27 |
| RU2468028C2 true RU2468028C2 (ru) | 2012-11-27 |
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| RU2009105399/04A RU2468028C2 (ru) | 2006-07-18 | 2007-07-17 | Спироциклические азаиндольные производные |
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| ES (1) | ES2434114T3 (enExample) |
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| RU (1) | RU2468028C2 (enExample) |
| WO (1) | WO2008009416A1 (enExample) |
| ZA (1) | ZA200901128B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102006033114A1 (de) | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| SI2271613T1 (sl) | 2008-03-27 | 2014-08-29 | Grunenthal Gmbh | Hidroksimetilcikloheksilamini |
| AR071066A1 (es) * | 2008-03-27 | 2010-05-26 | Gruenenthal Chemie | Derivados de (hetero) aril-ciclohexano |
| CA2719743A1 (en) | 2008-03-27 | 2009-10-01 | Gruenenthal Gmbh | Substituted cyclohexyldiamines |
| US8288430B2 (en) * | 2008-03-27 | 2012-10-16 | Grunenthal Gmbh | Spiro(5.5)undecane derivatives |
| RU2532545C2 (ru) | 2008-03-27 | 2014-11-10 | Грюненталь Гмбх | Замещенные производные 4-аминоциклогексана |
| TWI450899B (zh) * | 2008-03-27 | 2014-09-01 | 被取代之螺環環已烷衍生物 | |
| EP2575815A4 (en) | 2010-06-04 | 2013-12-25 | Albany Molecular Res Inc | GLYCIN TRANSPORTER 1 INHIBITORS, METHODS OF MAKING THE SAME, AND USES THEREOF |
| TWI582092B (zh) | 2010-07-28 | 2017-05-11 | 歌林達股份有限公司 | 順式－四氫－螺旋（環己烷－１,１’－吡啶［３,４－b］吲哚）－４－胺－衍生物 |
| AR084209A1 (es) | 2010-12-08 | 2013-05-02 | Gruenenthal Gmbh | Metodo para la sintesis de derivados de aminociclohexanona sustituidos |
| CA2942522A1 (en) * | 2014-03-12 | 2015-09-17 | The Trustees Of Columbia University In The City Of New York | 5,5-dioxo-11h-benzo[c][2,1]benzothiazepine derivatives and their use as mu-opioid receptor agonists |
| PL3169666T3 (pl) | 2014-07-15 | 2019-03-29 | Grünenthal GmbH | Podstawione pochodne azaspiro(4,5)dekanu |
| TW201607923A (zh) | 2014-07-15 | 2016-03-01 | 歌林達有限公司 | 被取代之氮螺環（４．５）癸烷衍生物 |
| WO2017049158A1 (en) | 2015-09-16 | 2017-03-23 | The Trustees Of Columbia University In The City Of New York | Carboxylic diarylthiazepineamines as mu-opioid receptor agonists |
| CN117447384B (zh) * | 2023-10-24 | 2024-12-27 | 四川大学 | 一种螺杂环芳基类化合物及其应用 |
Citations (5)
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|---|---|---|---|---|
| EP1142587A1 (en) * | 1998-12-24 | 2001-10-10 | Meiji Seika Kaisha Ltd. | Remedies for pain |
| RU2216737C1 (ru) * | 2002-03-19 | 2003-11-20 | Санкт-Петербургский государственный медицинский университет им. акад. И.П. Павлова | Способ оценки течения хронического воспалительного процесса в бронхолегочной системе больного муковисцидозом |
| WO2004043967A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische cyclohexan-derivate |
| WO2005063769A1 (de) * | 2003-12-23 | 2005-07-14 | Grünenthal GmbH | Spirocyclische cyclohexan-derivate |
| WO2005066183A1 (de) * | 2003-12-23 | 2005-07-21 | Grünenthal GmbH | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065573A (en) | 1976-06-03 | 1977-12-27 | The Upjohn Company | 4-Amino-4-phenylcyclohexanone ketal compositions and process of use |
| JPH06502147A (ja) * | 1990-10-09 | 1994-03-10 | ニューロゲン コーポレイション | 或る種のシクロアルキルおよびアザシクロアルキルピロロピリミジン；新規な種類のｇａｂａ脳リセプタリガンド |
| GB9918965D0 (en) * | 1999-08-11 | 1999-10-13 | Cerebrus Ltd | Chemical compounds xxi |
| EA005409B1 (ru) * | 2000-04-10 | 2005-02-24 | Пфайзер Продактс Инк. | Производные бензамидопиперидина в качестве антагонистов рецепторов вещества p |
| DE10123163A1 (de) | 2001-05-09 | 2003-01-16 | Gruenenthal Gmbh | Substituierte Cyclohexan-1,4-diaminderivate |
| EP1637521B1 (en) * | 2003-06-23 | 2013-06-19 | Ono Pharmaceutical Co., Ltd. | Novel tricyclic heterocycle compound |
| DE102004039382A1 (de) * | 2004-08-13 | 2006-02-23 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| CN101072771B (zh) * | 2004-10-07 | 2010-09-29 | 默沙东公司 | Cgrp受体拮抗剂 |
| EP1829874B1 (en) * | 2004-12-22 | 2014-02-12 | Ono Pharmaceutical Co., Ltd. | Tricyclic compound and use thereof |
| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102006019597A1 (de) * | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102006033114A1 (de) | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| DE102007009235A1 (de) * | 2007-02-22 | 2008-09-18 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007009319A1 (de) * | 2007-02-22 | 2008-08-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| TWI450899B (zh) * | 2008-03-27 | 2014-09-01 | 被取代之螺環環已烷衍生物 |
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2006
- 2006-07-18 DE DE102006033114A patent/DE102006033114A1/de not_active Withdrawn
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2007
- 2007-06-29 CL CL200701917A patent/CL2007001917A1/es unknown
- 2007-07-16 PE PE2007000917A patent/PE20080277A1/es active IP Right Grant
- 2007-07-16 AR ARP070103151A patent/AR062079A1/es not_active Application Discontinuation
- 2007-07-17 CA CA2658379A patent/CA2658379C/en not_active Expired - Fee Related
- 2007-07-17 ES ES07786123T patent/ES2434114T3/es active Active
- 2007-07-17 EP EP07786123.5A patent/EP2041142B1/de active Active
- 2007-07-17 AU AU2007276414A patent/AU2007276414B2/en not_active Ceased
- 2007-07-17 BR BRPI0714650-7A patent/BRPI0714650A2/pt not_active Application Discontinuation
- 2007-07-17 CN CN2007800272998A patent/CN101490055B/zh not_active Expired - Fee Related
- 2007-07-17 KR KR1020097003277A patent/KR101421034B1/ko not_active Expired - Fee Related
- 2007-07-17 MX MX2009000670A patent/MX2009000670A/es active IP Right Grant
- 2007-07-17 JP JP2009519861A patent/JP5269784B2/ja not_active Expired - Fee Related
- 2007-07-17 WO PCT/EP2007/006326 patent/WO2008009416A1/de not_active Ceased
- 2007-07-17 PL PL07786123T patent/PL2041142T3/pl unknown
- 2007-07-17 NZ NZ573688A patent/NZ573688A/en not_active IP Right Cessation
- 2007-07-17 RU RU2009105399/04A patent/RU2468028C2/ru not_active IP Right Cessation
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2009
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- 2009-01-19 NO NO20090294A patent/NO342282B1/no not_active IP Right Cessation
- 2009-02-17 ZA ZA2009/01128A patent/ZA200901128B/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1142587A1 (en) * | 1998-12-24 | 2001-10-10 | Meiji Seika Kaisha Ltd. | Remedies for pain |
| RU2216737C1 (ru) * | 2002-03-19 | 2003-11-20 | Санкт-Петербургский государственный медицинский университет им. акад. И.П. Павлова | Способ оценки течения хронического воспалительного процесса в бронхолегочной системе больного муковисцидозом |
| WO2004043967A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische cyclohexan-derivate |
| WO2005063769A1 (de) * | 2003-12-23 | 2005-07-14 | Grünenthal GmbH | Spirocyclische cyclohexan-derivate |
| WO2005066183A1 (de) * | 2003-12-23 | 2005-07-21 | Grünenthal GmbH | Spirocyclische cyclohexan-derivate mit affinität zum orl1-rezeptor |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20090294L (no) | 2009-03-31 |
| EP2041142A1 (de) | 2009-04-01 |
| JP5269784B2 (ja) | 2013-08-21 |
| MX2009000670A (es) | 2009-01-30 |
| IL196525A0 (en) | 2009-11-18 |
| NZ573688A (en) | 2011-12-22 |
| KR20090035708A (ko) | 2009-04-10 |
| PL2041142T3 (pl) | 2014-01-31 |
| CN101490055A (zh) | 2009-07-22 |
| BRPI0714650A2 (pt) | 2013-04-02 |
| RU2009105399A (ru) | 2010-08-27 |
| US20090156593A1 (en) | 2009-06-18 |
| ES2434114T3 (es) | 2013-12-13 |
| HK1129676A1 (en) | 2009-12-04 |
| WO2008009416A1 (de) | 2008-01-24 |
| US8399503B2 (en) | 2013-03-19 |
| AU2007276414A1 (en) | 2008-01-24 |
| AR062079A1 (es) | 2008-10-15 |
| JP2009543825A (ja) | 2009-12-10 |
| CA2658379C (en) | 2014-05-06 |
| AU2007276414B2 (en) | 2012-05-31 |
| DE102006033114A1 (de) | 2008-01-24 |
| EP2041142B1 (de) | 2013-10-09 |
| IL196525A (en) | 2015-07-30 |
| NO342282B1 (no) | 2018-04-30 |
| KR101421034B1 (ko) | 2014-07-22 |
| ZA200901128B (en) | 2009-12-30 |
| PE20080277A1 (es) | 2008-04-11 |
| CN101490055B (zh) | 2013-10-16 |
| CL2007001917A1 (es) | 2008-03-14 |
| CA2658379A1 (en) | 2008-01-24 |
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