JPH0577652B2 - - Google Patents

Info

Publication number: JPH0577652B2
Authority: JP; Japan
Prior art keywords: group; pyridyl; brain metabolism; metabolism activator; chlorophenyl
Prior art date: 1988-05-13
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.): Expired - Lifetime

Application number

JP10856089A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0249725A (ja

Inventor

Mikio Takeda

Masaru Inage

Hiroshi Wada

Takashi Ochiai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tanabe Seiyaku Co Ltd

Original Assignee

Tanabe Seiyaku Co Ltd

Priority date (The priority date 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 date listed.)

1988-05-13

Filing date

1989-04-27

Publication date

1993-10-27

1989-04-27 Application filed by Tanabe Seiyaku Co Ltd filed Critical Tanabe Seiyaku Co Ltd

1990-02-20 Publication of JPH0249725A publication Critical patent/JPH0249725A/ja

1993-10-27 Publication of JPH0577652B2 publication Critical patent/JPH0577652B2/ja

Status Granted legal-status Critical Current

Links

-1 methoxyphenyl group Chemical group 0.000 claims description 27
210000004556 brain Anatomy 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 20
230000004060 metabolic process Effects 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 13
239000012190 activator Substances 0.000 claims description 13
150000008624 imidazolidinones Chemical class 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
230000003247 decreasing effect Effects 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
208000024827 Alzheimer disease Diseases 0.000 claims description 2
208000027534 Emotional disease Diseases 0.000 claims description 2
208000026139 Memory disease Diseases 0.000 claims description 2
206010039966 Senile dementia Diseases 0.000 claims description 2
230000004913 activation Effects 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000006383 alkylpyridyl group Chemical group 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
230000003111 delayed effect Effects 0.000 claims description 2
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
208000011977 language disease Diseases 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000006384 methylpyridyl group Chemical group 0.000 claims description 2
230000008450 motivation Effects 0.000 claims description 2
231100000862 numbness Toxicity 0.000 claims description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
230000003449 preventive effect Effects 0.000 claims 3
230000001225 therapeutic effect Effects 0.000 claims 3
HZKKPRUXOCZMBT-UXBLZVDNSA-N 1-(6-methylpyridin-2-yl)-3-[(e)-3-phenylprop-2-enyl]imidazolidin-2-one Chemical compound CC1=CC=CC(N2C(N(C\C=C\C=3C=CC=CC=3)CC2)=O)=N1 HZKKPRUXOCZMBT-UXBLZVDNSA-N 0.000 claims 1
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000001816 cooling Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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229920002134 Carboxymethyl cellulose Polymers 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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238000001035 drying Methods 0.000 description 4
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JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
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DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
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239000000126 substance Substances 0.000 description 3
GHKZUTAGOUFZGD-UHFFFAOYSA-N 1-(2-chloroethyl)-3-pyridin-3-ylurea Chemical compound ClCCNC(=O)NC1=CC=CN=C1 GHKZUTAGOUFZGD-UHFFFAOYSA-N 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
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UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 2
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 2
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 2
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
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OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
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238000010304 firing Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
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239000005457 ice water Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
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229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000463 material Substances 0.000 description 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
HVEQXZIFRYMVFL-UHFFFAOYSA-N n'-(pyridin-3-ylmethyl)ethane-1,2-diamine Chemical compound NCCNCC1=CC=CN=C1 HVEQXZIFRYMVFL-UHFFFAOYSA-N 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
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
210000000449 purkinje cell Anatomy 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
210000003568 synaptosome Anatomy 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP10856089A 1988-05-13 1989-04-27 脳代謝賦活剤 Granted JPH0249725A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP63-117844		1988-05-13
JP11784488		1988-05-13

Publications (2)

Publication Number	Publication Date
JPH0249725A JPH0249725A (ja)	1990-02-20
JPH0577652B2 true JPH0577652B2 (fr)	1993-10-27

Family

ID=14721670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10856089A Granted JPH0249725A (ja)	1988-05-13	1989-04-27	脳代謝賦活剤

Country Status (1)

Country	Link
JP (1)	JPH0249725A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2373685A1 (fr)	1999-05-19	2000-11-23	The Procter & Gamble Company	Procede de preparation de composes oxazolidinone fonctionnalises
KR100378748B1 (ko) *	1999-12-17	2003-04-07	한미약품공업 주식회사	말톨릴 파라-쿠마레이트, 이의 제조 방법 및 이를포함하는 치매 치료용 조성물
MX2010014572A (es)	2008-06-27	2011-03-24	Novartis Ag	Compuestos organicos.

1989
- 1989-04-27 JP JP10856089A patent/JPH0249725A/ja active Granted

Also Published As

Publication number	Publication date
JPH0249725A (ja)	1990-02-20

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US5001134A (en)	1991-03-19	Piperidines, processes of preparation and medications containing them
EP0268229B1 (fr)	1992-07-08	Composés d'imidazolidinone, leurs procédés de preéparation, composition les contenant, et leur utilisation pour fabrication de médicaments ayant une valeur thérapeutique
JPS6053014B2 (ja)	1985-11-22	薬理作用を有するピリジン誘導体
RU2165420C2 (ru)	2001-04-20	1,2,5-тиадиазольные производные индолилалкил-пиримидинил-пиперазинов и фармацевтическая композиция на их основе
EP0816338B1 (fr)	2003-02-12	Derives de 3-(bis-phenylmethylene substitue) oxindole
US20040087604A1 (en)	2004-05-06	Hetero-tricyclic compounds having substituted amino groups
JPH0577652B2 (fr)	1993-10-27
PT78491B (en)	1986-05-22	Process for the preparation of new 5-acyl-2-(1h)-pyridinones useful as cardiotonic agents
KR100191386B1 (ko)	1999-06-15	3-(1,2-벤즈이속사졸-3-일)-4-피리딘아민 및 유도체,이를 함유하는 약제학적 조성물 및 이의 제조방법
EP0505481A1 (fr)	1992-09-30	4,5-diphenyle-imidazoles substituees en position 2
US5179099A (en)	1993-01-12	2,3-dihydro-1-(pyridinylamino)-indoles
CZ658590A3 (en)	1997-05-14	Aminopyridinylmethanols, aminomethylpyridinamines and their derivatives, process of their preparation, pharmaceutical composition containing such compounds and use thereof
US4486431A (en)	1984-12-04	Cardiotonic use of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinones
US5296488A (en)	1994-03-22	Method of using 2,3-dihydro-1-(pyridinylamino)-indoles as anticonvulsants and for the enhancement of memory
EP0038003A2 (fr)	1981-10-21	Pyrrolylpipéridines comme antidépresseurs
JPS62226977A (ja)	1987-10-05	ピリジン誘導体
JPH04305557A (ja)	1992-10-28	置換アニリド