NZ535641A - Novel azacyclic ethynyl derivatives - Google Patents
Novel azacyclic ethynyl derivativesInfo
- Publication number
- NZ535641A NZ535641A NZ535641A NZ53564103A NZ535641A NZ 535641 A NZ535641 A NZ 535641A NZ 535641 A NZ535641 A NZ 535641A NZ 53564103 A NZ53564103 A NZ 53564103A NZ 535641 A NZ535641 A NZ 535641A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- alkyl
- cycloalkyl
- alkenyl
- cycloalkoxy
- Prior art date
Links
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- -1 cyano, amino Chemical group 0.000 claims description 178
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 58
- 125000000304 alkynyl group Chemical group 0.000 claims description 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
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- 125000003342 alkenyl group Chemical group 0.000 claims description 36
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
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- FYQFXHPDTCMLMY-UHFFFAOYSA-N 8-methyl-3-(2-methylbut-1-en-3-ynyl)-8-azabicyclo[3.2.1]oct-3-ene Chemical compound C1C(C=C(C)C#C)=CC2CCC1N2C FYQFXHPDTCMLMY-UHFFFAOYSA-N 0.000 claims description 2
- MKSXUVTXJXBGNV-UHFFFAOYSA-N 8-methyl-3-(3-phenylprop-1-ynyl)-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C(C2)CCC1C=C2C#CCC1=CC=CC=C1 MKSXUVTXJXBGNV-UHFFFAOYSA-N 0.000 claims description 2
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- 238000002372 labelling Methods 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OIRDBPQYVWXNSJ-BJUDXGSMSA-N methyl trifluoromethanesulfonate Chemical compound [11CH3]OS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-BJUDXGSMSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
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- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
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- 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 1
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- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
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- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 150000004291 polyenes Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 239000000651 prodrug Substances 0.000 description 1
- GHUURDQYRGVEHX-UHFFFAOYSA-N prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC=C1 GHUURDQYRGVEHX-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
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- 239000002435 venom Substances 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Addiction (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200200691 | 2002-05-07 | ||
| PCT/DK2003/000294 WO2003094830A2 (en) | 2002-05-07 | 2003-05-06 | Novel azacyclic ethynyl derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ535641A true NZ535641A (en) | 2006-10-27 |
Family
ID=29414627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ535641A NZ535641A (en) | 2002-05-07 | 2003-05-06 | Novel azacyclic ethynyl derivatives |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7378526B2 (enExample) |
| EP (1) | EP1506205B1 (enExample) |
| JP (1) | JP2005524712A (enExample) |
| CN (1) | CN100522976C (enExample) |
| AT (1) | ATE401334T1 (enExample) |
| AU (1) | AU2003222738B2 (enExample) |
| CA (1) | CA2480378A1 (enExample) |
| DE (1) | DE60322212D1 (enExample) |
| MX (1) | MXPA04010965A (enExample) |
| NZ (1) | NZ535641A (enExample) |
| WO (1) | WO2003094830A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| CA2499128C (en) | 2002-09-25 | 2012-07-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| PL1697378T3 (pl) | 2003-12-22 | 2008-04-30 | Memory Pharm Corp | Indole, 1h-indazole, 1,2-benzoizoksazole i 1,2-benzoizotiazole oraz ich wytwarzanie i zastosowania |
| WO2005092890A2 (en) | 2004-03-25 | 2005-10-06 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| DE602005024677D1 (de) | 2004-04-22 | 2010-12-23 | Memory Pharm Corp | Indole, 1h-indazole, 1,2-benzisoxazole, 1,2-benzoisothiazole, deren herstellung und verwendungen |
| RU2386633C2 (ru) | 2004-05-07 | 2010-04-20 | Мемори Фармасьютиклз Корпорейшн | 1h-индазолы, бензотиазолы, 1, 2-бензоизоксазолы, 1, 2-бензоизотиазолы и хромоны и их получение и применения |
| JP2008525464A (ja) | 2004-12-22 | 2008-07-17 | メモリー・ファーマシューティカルズ・コーポレイション | α−７ニコチン性受容体リガンド並びにその製造及び使用 |
| AU2010319927B2 (en) * | 2009-10-29 | 2015-01-22 | Janssen Pharmaceutica Nv | Alkynyl derivatives useful as DPP-1 inhibitors |
| TWI519532B (zh) | 2010-05-17 | 2016-02-01 | 艾維沃製藥公司 | （Ｒ）－７－氯－Ｎ－（啶－３－基）苯並［b］噻吩－２－羧醯胺鹽酸鹽單水合物之結晶形體 |
| RU2017136693A (ru) | 2012-05-08 | 2019-02-08 | Форум Фармасьютикалз, Инк. | Способы поддержания, лечения или улучшения когнитивной функции |
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| GB9218334D0 (en) * | 1992-08-28 | 1992-10-14 | Ici Plc | Heterocyclic compounds |
| GB9226573D0 (en) * | 1992-12-21 | 1993-02-17 | Ici Plc | Heterocyclic compounds |
| US5616712A (en) * | 1995-05-16 | 1997-04-01 | Allergan | Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-thio-1,2,3,4-tetrahdroquinolinyl, 2-alkylthio-3,4-dihydroquinolinyl or 2-alkoxy-3,4-dihydroquinolinyl group having retinoid-like biological activity |
| HUP9802433A3 (en) * | 1995-10-13 | 2000-03-28 | Neurosearch As | 8-azabicyclo[3.2.1]oct-2-ene derivatives, their preparation and use |
| KR100589872B1 (ko) * | 1997-05-30 | 2006-06-15 | 뉴로서치 에이/에스 | 8-아자비사이클로(3,2,1)옥트-2-엔 유도체 및 이의 제조방법 |
| DE69914935T2 (de) * | 1998-11-27 | 2009-10-01 | Neurosearch A/S | 8-azabicyclo[3.2.1]okt-2-en- und -oktanderivate |
| UA71945C2 (en) * | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| JP4815083B2 (ja) | 1999-08-31 | 2011-11-16 | メルク・シャープ・エンド・ドーム・コーポレイション | 複素環化合物およびそれの使用方法 |
| JP5154728B2 (ja) * | 2000-07-24 | 2013-02-27 | クレニツキー・ファーマシューティカルズ，インコーポレイテッド | 神経栄養活性を有する置換５−アルキニルピリミジン |
| US6624167B1 (en) * | 2000-08-04 | 2003-09-23 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| EP1358177B1 (en) * | 2000-10-13 | 2006-08-02 | NeuroSearch A/S | Treatment of affective disorders by the combined action of a nicotinic receptor agonist and a monoaminergic substance |
| RU2288919C2 (ru) * | 2001-10-02 | 2006-12-10 | Акадиа Фармасьютикалз, Инк. | Производные бензимидазолидинона в качестве агентов мускариновых рецепторов |
| RU2004110717A (ru) | 2001-10-17 | 2005-10-20 | Юсиби, С.А. (Be) | Производные хинуклидина, способы их получения и их применение в качестве и нгибиторов м2- и/или м3- мускариновых рецепторов |
| KR100432283B1 (ko) * | 2001-10-27 | 2004-05-22 | 한국과학기술연구원 | 무스카린성 아세틸콜린 수용체에 작용하는테트라하이드로피리딘 유도체 |
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2003
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- 2003-05-06 MX MXPA04010965A patent/MXPA04010965A/es active IP Right Grant
- 2003-05-06 DE DE60322212T patent/DE60322212D1/de not_active Expired - Lifetime
- 2003-05-06 NZ NZ535641A patent/NZ535641A/en not_active IP Right Cessation
- 2003-05-06 CN CNB03810184XA patent/CN100522976C/zh not_active Expired - Fee Related
- 2003-05-06 CA CA002480378A patent/CA2480378A1/en not_active Abandoned
- 2003-05-06 WO PCT/DK2003/000294 patent/WO2003094830A2/en not_active Ceased
- 2003-05-06 EP EP03718655A patent/EP1506205B1/en not_active Expired - Lifetime
- 2003-05-06 AT AT03718655T patent/ATE401334T1/de not_active IP Right Cessation
- 2003-05-06 US US10/513,416 patent/US7378526B2/en not_active Expired - Fee Related
- 2003-05-06 JP JP2004502919A patent/JP2005524712A/ja not_active Ceased
-
2008
- 2008-03-25 US US12/076,929 patent/US7667040B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7667040B2 (en) | 2010-02-23 |
| ATE401334T1 (de) | 2008-08-15 |
| WO2003094830A2 (en) | 2003-11-20 |
| WO2003094830A3 (en) | 2004-03-18 |
| US20050171078A1 (en) | 2005-08-04 |
| US7378526B2 (en) | 2008-05-27 |
| CN100522976C (zh) | 2009-08-05 |
| CN1649884A (zh) | 2005-08-03 |
| JP2005524712A (ja) | 2005-08-18 |
| DE60322212D1 (de) | 2008-08-28 |
| US20080188519A1 (en) | 2008-08-07 |
| EP1506205B1 (en) | 2008-07-16 |
| HK1079528A1 (en) | 2006-04-07 |
| AU2003222738B2 (en) | 2009-09-17 |
| MXPA04010965A (es) | 2005-01-25 |
| AU2003222738A1 (en) | 2003-11-11 |
| CA2480378A1 (en) | 2003-11-20 |
| EP1506205A2 (en) | 2005-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |