JP2007536262A5 - - Google Patents
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- Publication number
- JP2007536262A5 JP2007536262A5 JP2007511639A JP2007511639A JP2007536262A5 JP 2007536262 A5 JP2007536262 A5 JP 2007536262A5 JP 2007511639 A JP2007511639 A JP 2007511639A JP 2007511639 A JP2007511639 A JP 2007511639A JP 2007536262 A5 JP2007536262 A5 JP 2007536262A5
- Authority
- JP
- Japan
- Prior art keywords
- unsubstituted
- substituted
- alkyl
- group
- aryl
- 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.)
- Granted
Links
- 208000015114 central nervous system disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 206010010904 Convulsion Diseases 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 208000005298 acute pain Diseases 0.000 claims description 2
- 230000037328 acute stress Effects 0.000 claims description 2
- 230000007278 cognition impairment Effects 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 206010022437 insomnia Diseases 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 150
- 125000001072 heteroaryl group Chemical group 0.000 claims 80
- 125000005843 halogen group Chemical group 0.000 claims 58
- 125000003118 aryl group Chemical group 0.000 claims 53
- 125000003545 alkoxy group Chemical group 0.000 claims 51
- 125000003710 aryl alkyl group Chemical group 0.000 claims 50
- 229910052739 hydrogen Inorganic materials 0.000 claims 48
- 239000001257 hydrogen Substances 0.000 claims 48
- -1 respectively Chemical group 0.000 claims 44
- 125000003107 substituted aryl group Chemical group 0.000 claims 42
- 125000000304 alkynyl group Chemical group 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 34
- 150000002431 hydrogen Chemical class 0.000 claims 30
- 125000003282 alkyl amino group Chemical group 0.000 claims 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 27
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims 25
- 125000004104 aryloxy group Chemical group 0.000 claims 24
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 24
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 24
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 24
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 24
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 24
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 14
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 230000001548 androgenic effect Effects 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- PYSGLBRHUGMASW-UHFFFAOYSA-N 3-(4-ethynylanilino)-2-(naphthalene-1-carbonyl)-n-propylprop-2-enamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)C(C(=O)NCCC)=CNC1=CC=C(C#C)C=C1 PYSGLBRHUGMASW-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 230000036461 convulsion Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- PULIYOGSPNXUJG-UHFFFAOYSA-N 2-(2-chlorobenzoyl)-3-(4-cyanoanilino)-n-ethylprop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NCC)=CNC1=CC=C(C#N)C=C1 PULIYOGSPNXUJG-UHFFFAOYSA-N 0.000 claims 1
- VNFHKLZFPHDSOC-UHFFFAOYSA-N 2-(2-chlorobenzoyl)-3-(4-cyanoanilino)-n-propylprop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NCCC)=CNC1=CC=C(C#N)C=C1 VNFHKLZFPHDSOC-UHFFFAOYSA-N 0.000 claims 1
- PWISUYLWWRGATH-UHFFFAOYSA-N 2-(2-chlorobenzoyl)-3-(4-ethoxyanilino)-n-ethylprop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NCC)=CNC1=CC=C(OCC)C=C1 PWISUYLWWRGATH-UHFFFAOYSA-N 0.000 claims 1
- AJLSSIGLWUMOCU-UHFFFAOYSA-N 2-(2-chlorobenzoyl)-3-(4-ethynylanilino)-n-propylprop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NCCC)=CNC1=CC=C(C#C)C=C1 AJLSSIGLWUMOCU-UHFFFAOYSA-N 0.000 claims 1
- ARFYCKPFAZQVJU-UHFFFAOYSA-N 2-(2-chlorobenzoyl)-3-(4-iodoanilino)-n-methylprop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NC)=CNC1=CC=C(I)C=C1 ARFYCKPFAZQVJU-UHFFFAOYSA-N 0.000 claims 1
- JIRQMMIZNXRDNV-UHFFFAOYSA-N 2-(2-chlorobenzoyl)-3-(4-iodoanilino)-n-prop-2-ynylprop-2-enamide Chemical compound ClC1=CC=CC=C1C(=O)C(C(=O)NCC#C)=CNC1=CC=C(I)C=C1 JIRQMMIZNXRDNV-UHFFFAOYSA-N 0.000 claims 1
- OCPNZNIKSBMCTD-UHFFFAOYSA-N 2-(2-chlorobenzoyl)-n-ethyl-3-(1-phenylethylamino)prop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NCC)=CNC(C)C1=CC=CC=C1 OCPNZNIKSBMCTD-UHFFFAOYSA-N 0.000 claims 1
- MSFPCACOZLJKPW-UHFFFAOYSA-N 2-(2-chlorobenzoyl)-n-ethyl-3-(4-iodoanilino)prop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NCC)=CNC1=CC=C(I)C=C1 MSFPCACOZLJKPW-UHFFFAOYSA-N 0.000 claims 1
- DPNDQKSLRMCTQF-UHFFFAOYSA-N 2-benzoyl-3-(4-chloroanilino)-n-propan-2-ylprop-2-enamide Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)NC(C)C)=CNC1=CC=C(Cl)C=C1 DPNDQKSLRMCTQF-UHFFFAOYSA-N 0.000 claims 1
- RFEYESZEAQAUBZ-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-ethyl-3-oxo-2-(pyrazin-2-ylamino)propanamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NCC)NC1=CN=CC=N1 RFEYESZEAQAUBZ-UHFFFAOYSA-N 0.000 claims 1
- APRHUUXIKCFSHX-UHFFFAOYSA-N 3-(4-chloroanilino)-2-(2-chlorobenzoyl)-n-propan-2-ylprop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NC(C)C)=CNC1=CC=C(Cl)C=C1 APRHUUXIKCFSHX-UHFFFAOYSA-N 0.000 claims 1
- BWGOHMRTABFJSA-UHFFFAOYSA-N 3-(4-chloroanilino)-2-(2-chlorobenzoyl)-n-propylprop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NCCC)=CNC1=CC=C(Cl)C=C1 BWGOHMRTABFJSA-UHFFFAOYSA-N 0.000 claims 1
- USOXBMZFVFXTDW-UHFFFAOYSA-N 3-(4-cyanoanilino)-2-(2-methylbenzoyl)-n-propylprop-2-enamide Chemical compound C=1C=CC=C(C)C=1C(=O)C(C(=O)NCCC)=CNC1=CC=C(C#N)C=C1 USOXBMZFVFXTDW-UHFFFAOYSA-N 0.000 claims 1
- URBQXIBZGNGCOC-UHFFFAOYSA-N 3-(4-ethynylanilino)-2-(2-methylbenzoyl)-n-prop-2-ynylprop-2-enamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=O)NCC#C)=CNC1=CC=C(C#C)C=C1 URBQXIBZGNGCOC-UHFFFAOYSA-N 0.000 claims 1
- ZVKLQQRYCUNZEV-UHFFFAOYSA-N 3-(4-ethynylanilino)-2-(2-methylbenzoyl)-n-propylprop-2-enamide Chemical compound C=1C=CC=C(C)C=1C(=O)C(C(=O)NCCC)=CNC1=CC=C(C#C)C=C1 ZVKLQQRYCUNZEV-UHFFFAOYSA-N 0.000 claims 1
- VYIBCOSBNVFEIW-UHFFFAOYSA-N 3-phenylpropanamide Chemical compound NC(=O)CCC1=CC=CC=C1 VYIBCOSBNVFEIW-UHFFFAOYSA-N 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000016588 Idiopathic hypersomnia Diseases 0.000 claims 1
- 206010029333 Neurosis Diseases 0.000 claims 1
- 206010062519 Poor quality sleep Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 230000007000 age related cognitive decline Effects 0.000 claims 1
- 150000001356 alkyl thiols Chemical class 0.000 claims 1
- 230000037007 arousal Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- MZWNWTVGHFVCBO-UHFFFAOYSA-N n-butan-2-yl-3-(4-chloroanilino)-2-(2-chlorobenzoyl)prop-2-enamide Chemical compound C=1C=CC=C(Cl)C=1C(=O)C(C(=O)NC(C)CC)=CNC1=CC=C(Cl)C=C1 MZWNWTVGHFVCBO-UHFFFAOYSA-N 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000015238 neurotic disease Diseases 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 208000019899 phobic disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 231100000736 substance abuse Toxicity 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 206010011224 Cough Diseases 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56946504P | 2004-05-06 | 2004-05-06 | |
| US60/569,465 | 2004-05-06 | ||
| PCT/US2005/015869 WO2005108347A2 (en) | 2004-05-06 | 2005-05-05 | Substituted enaminones, their derivatives and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007536262A JP2007536262A (ja) | 2007-12-13 |
| JP2007536262A5 true JP2007536262A5 (OSRAM) | 2011-07-14 |
| JP5002452B2 JP5002452B2 (ja) | 2012-08-15 |
Family
ID=35320783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007511639A Expired - Fee Related JP5002452B2 (ja) | 2004-05-06 | 2005-05-05 | 置換エナミノン類、それらの誘導体およびそれらの使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7825278B2 (OSRAM) |
| EP (1) | EP1742904B1 (OSRAM) |
| JP (1) | JP5002452B2 (OSRAM) |
| CN (1) | CN1976892A (OSRAM) |
| AU (1) | AU2005240657A1 (OSRAM) |
| BR (1) | BRPI0510715A (OSRAM) |
| CA (1) | CA2565627A1 (OSRAM) |
| IL (1) | IL179068A0 (OSRAM) |
| MX (1) | MXPA06012839A (OSRAM) |
| NO (1) | NO20065595L (OSRAM) |
| RU (1) | RU2006142896A (OSRAM) |
| UA (1) | UA85711C2 (OSRAM) |
| WO (1) | WO2005108347A2 (OSRAM) |
| ZA (1) | ZA200609924B (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006138510A1 (en) * | 2005-06-17 | 2006-12-28 | The Regents Of The University Of California | Substituted enaminones as nicotinic acetylcholine receptor modulators |
| US8110588B2 (en) | 2007-08-08 | 2012-02-07 | Neurosearch A/S | 1,2,3-triazole derivatives useful as modulators of nicotinic acetylcholine receptors |
| JP2011514906A (ja) * | 2008-03-11 | 2011-05-12 | ノイロサーチ アクティーゼルスカブ | ニコチン性アセチルコリン受容体のモジュレーターとして有用な新規の１，２，３−トリアゾール誘導体 |
| CA2733499A1 (en) * | 2008-08-08 | 2010-02-11 | Neurosearch A/S | Novel diphenyl 1,2,3-triazole derivatives useful as modulators of nicotinic acetylcholine receptors |
| PT3311666T (pt) | 2010-08-18 | 2021-06-21 | Biosplice Therapeutics Inc | Dicetonas e hidroxicetonas como ativadores da via de sinalização de catenina |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| SG10201606032VA (en) | 2013-02-22 | 2016-09-29 | Samumed Llc | Gamma-Diketones As Wnt/Beta -Catenin Signaling Pathway Activators |
| CN107106549B (zh) | 2014-08-20 | 2020-06-16 | 萨穆梅德有限公司 | 用于治疗和预防老化皮肤和皱纹的γ–二酮 |
| AR115966A1 (es) | 2018-08-17 | 2021-03-17 | Pi Industries Ltd | Compuestos de fenilamidina y sus usos |
| CN112321451B (zh) * | 2019-12-13 | 2022-08-23 | 福建海西新药创制有限公司 | 一种用于制备盐酸西那卡塞药物中间体的方法 |
| CN113354530B (zh) * | 2020-03-07 | 2025-11-18 | 东莞市东阳光动物保健药品有限公司 | 一种制备4-乙酰基-1-萘甲酸的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252951A (en) * | 1979-10-09 | 1981-02-24 | Eli Lilly And Company | Isolation of syn-7-(2-amino-4-thiazolyl)-(methoxyimino)acetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid |
| FR2639636B1 (fr) | 1988-11-30 | 1994-03-04 | Novapharme | Nouveaux composes heterocycliques a activite anticonvulsivante, procede de preparation et compositions therapeutiques les contenant |
| US5318965A (en) * | 1990-08-24 | 1994-06-07 | Abbott Laboratories | Quinobenzoxazine, antineoplastic agents |
| WO1993013091A1 (fr) * | 1991-12-27 | 1993-07-08 | Wakunaga Seiyaku Kabushiki Kaisha | Nouveau derive de quinolone ou sel de ce derive et agent antibacterien contenant ce derive |
| ES2049640B1 (es) | 1992-06-18 | 1994-12-16 | Genesis Para La Investigacion | Procedimiento paras la preparacion de acidos quinolin carboxilicos. |
| US5622967A (en) * | 1993-04-26 | 1997-04-22 | Sterling Winthrop, Inc. | Quinolone carboxamide Calpain inhibitors |
| TW273551B (OSRAM) * | 1993-05-24 | 1996-04-01 | Wakiei Seiyaku Kk | |
| GB9706730D0 (en) * | 1997-04-03 | 1997-05-21 | Pharmacia & Upjohn Spa | 2-[(3-substituted)-5-Isoxazolymethylaminojalkanamid derivatives |
| GB9817118D0 (en) | 1998-08-07 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| EP1503759B1 (en) * | 2002-05-14 | 2008-12-17 | The Regents Of The University Of California | Substituted quinolone carboxylic acids, their derivatives, site of action, and uses thereof |
-
2005
- 2005-05-05 UA UAA200612755A patent/UA85711C2/ru unknown
- 2005-05-05 CA CA002565627A patent/CA2565627A1/en not_active Abandoned
- 2005-05-05 EP EP05750643A patent/EP1742904B1/en not_active Expired - Lifetime
- 2005-05-05 BR BRPI0510715-6A patent/BRPI0510715A/pt not_active IP Right Cessation
- 2005-05-05 CN CNA2005800214141A patent/CN1976892A/zh active Pending
- 2005-05-05 ZA ZA200609924A patent/ZA200609924B/xx unknown
- 2005-05-05 MX MXPA06012839A patent/MXPA06012839A/es unknown
- 2005-05-05 JP JP2007511639A patent/JP5002452B2/ja not_active Expired - Fee Related
- 2005-05-05 US US11/123,597 patent/US7825278B2/en not_active Expired - Fee Related
- 2005-05-05 AU AU2005240657A patent/AU2005240657A1/en not_active Abandoned
- 2005-05-05 WO PCT/US2005/015869 patent/WO2005108347A2/en not_active Ceased
- 2005-05-05 RU RU2006142896/04A patent/RU2006142896A/ru not_active Application Discontinuation
-
2006
- 2006-11-06 IL IL179068A patent/IL179068A0/en unknown
- 2006-12-05 NO NO20065595A patent/NO20065595L/no not_active Application Discontinuation
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