NO300130B1 - 1-fenylpyrrolidon-derivater med optisk aktivitet, mellomprodukt for fremstilling derav, et fölgeprodukt derav, en farmasöytisk blanding inneholdende dette, samt anvendelse av dette - Google Patents
1-fenylpyrrolidon-derivater med optisk aktivitet, mellomprodukt for fremstilling derav, et fölgeprodukt derav, en farmasöytisk blanding inneholdende dette, samt anvendelse av dette Download PDFInfo
- Publication number
- NO300130B1 NO300130B1 NO941757A NO941757A NO300130B1 NO 300130 B1 NO300130 B1 NO 300130B1 NO 941757 A NO941757 A NO 941757A NO 941757 A NO941757 A NO 941757A NO 300130 B1 NO300130 B1 NO 300130B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- butylphenyl
- pyrrolidon
- group
- Prior art date
Links
- 230000003287 optical effect Effects 0.000 title claims description 22
- JMVIVASFFKKFQK-UHFFFAOYSA-N 1-phenylpyrrolidin-2-one Chemical class O=C1CCCN1C1=CC=CC=C1 JMVIVASFFKKFQK-UHFFFAOYSA-N 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 26
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical group CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- ZPWDKFLAMVCCET-OAHLLOKOSA-N 4-[(3s)-1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC([C@@H]2CC(=O)N(C2)C=2C=CC(=CC=2)C(C)(C)C)=C1 ZPWDKFLAMVCCET-OAHLLOKOSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- YZADMDZNVOBYGR-HNNXBMFYSA-N 4-[[(3s)-1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]methoxy]benzoic acid Chemical group C1=CC(C(C)(C)C)=CC=C1N1C(=O)C[C@H](COC=2C=CC(=CC=2)C(O)=O)C1 YZADMDZNVOBYGR-HNNXBMFYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- JVTZOQMDKZFRBJ-INIZCTEOSA-N methyl 4-[[(3s)-1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]methoxy]benzoate Chemical group C1=CC(C(=O)OC)=CC=C1OC[C@H]1CC(=O)N(C=2C=CC(=CC=2)C(C)(C)C)C1 JVTZOQMDKZFRBJ-INIZCTEOSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- 230000000694 effects Effects 0.000 abstract description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
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- 230000035484 reaction time Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24288792 | 1992-09-11 | ||
| PCT/JP1993/001274 WO1994006767A1 (fr) | 1992-09-11 | 1993-09-08 | Derive de 1-phenylpyrrolidone a activite optique, intermediaire permettant de le produire, et leurs procedes de production |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO941757D0 NO941757D0 (no) | 1994-05-10 |
| NO941757L NO941757L (no) | 1994-05-10 |
| NO300130B1 true NO300130B1 (no) | 1997-04-14 |
Family
ID=17095708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO941757A NO300130B1 (no) | 1992-09-11 | 1994-05-10 | 1-fenylpyrrolidon-derivater med optisk aktivitet, mellomprodukt for fremstilling derav, et fölgeprodukt derav, en farmasöytisk blanding inneholdende dette, samt anvendelse av dette |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5475118A (ja) |
| EP (2) | EP0627419B1 (ja) |
| JP (1) | JP2724634B2 (ja) |
| KR (1) | KR0141657B1 (ja) |
| AT (2) | ATE186907T1 (ja) |
| AU (1) | AU663233B2 (ja) |
| CA (1) | CA2122705C (ja) |
| DE (2) | DE69333903T2 (ja) |
| DK (1) | DK0627419T3 (ja) |
| ES (2) | ES2247657T3 (ja) |
| FI (2) | FI107605B (ja) |
| HU (1) | HU215598B (ja) |
| NO (1) | NO300130B1 (ja) |
| WO (1) | WO1994006767A1 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69928749T2 (de) * | 1998-02-24 | 2006-06-29 | Taiho Pharmaceutical Co. Ltd. | Lp(a)-Senkendes Mittel und die Apolipoprotein(a)-Bildung unterdrückendes Mittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0393607T3 (da) * | 1989-04-19 | 1996-03-18 | Otsuka Pharma Co Ltd | Phenylcarboxylsyrederivater med en heteroring |
| JPH06192221A (ja) * | 1992-12-25 | 1994-07-12 | Taiho Yakuhin Kogyo Kk | 光学活性な１−（４−ｔ−ブチルフェニル）−５−オキソ−３−ピロリジンカルボン酸の製造方法 |
-
1993
- 1993-09-08 HU HU9401470A patent/HU215598B/hu not_active IP Right Cessation
- 1993-09-08 EP EP93919628A patent/EP0627419B1/en not_active Expired - Lifetime
- 1993-09-08 KR KR1019940701558A patent/KR0141657B1/ko not_active Expired - Fee Related
- 1993-09-08 DE DE69333903T patent/DE69333903T2/de not_active Expired - Fee Related
- 1993-09-08 ES ES98203959T patent/ES2247657T3/es not_active Expired - Lifetime
- 1993-09-08 DK DK93919628T patent/DK0627419T3/da active
- 1993-09-08 AU AU49832/93A patent/AU663233B2/en not_active Ceased
- 1993-09-08 DE DE69327092T patent/DE69327092T2/de not_active Expired - Fee Related
- 1993-09-08 AT AT93919628T patent/ATE186907T1/de not_active IP Right Cessation
- 1993-09-08 ES ES93919628T patent/ES2139670T3/es not_active Expired - Lifetime
- 1993-09-08 EP EP98203959A patent/EP0916657B9/en not_active Expired - Lifetime
- 1993-09-08 US US08/211,950 patent/US5475118A/en not_active Expired - Fee Related
- 1993-09-08 WO PCT/JP1993/001274 patent/WO1994006767A1/ja not_active Ceased
- 1993-09-08 AT AT98203959T patent/ATE309212T1/de not_active IP Right Cessation
- 1993-09-08 JP JP6507962A patent/JP2724634B2/ja not_active Expired - Lifetime
- 1993-09-08 CA CA002122705A patent/CA2122705C/en not_active Expired - Fee Related
-
1994
- 1994-05-10 FI FI942167A patent/FI107605B/fi active
- 1994-05-10 NO NO941757A patent/NO300130B1/no unknown
-
2000
- 2000-08-28 FI FI20001893A patent/FI108130B/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| DE69327092D1 (de) | 1999-12-30 |
| NO941757D0 (no) | 1994-05-10 |
| CA2122705A1 (en) | 1994-03-31 |
| KR0141657B1 (ko) | 1998-06-01 |
| ATE186907T1 (de) | 1999-12-15 |
| EP0916657B9 (en) | 2006-05-17 |
| CA2122705C (en) | 1997-11-18 |
| FI942167A0 (fi) | 1994-05-10 |
| AU663233B2 (en) | 1995-09-28 |
| HU9401470D0 (en) | 1994-08-29 |
| US5475118A (en) | 1995-12-12 |
| DE69327092T2 (de) | 2000-05-25 |
| EP0627419A4 (en) | 1995-02-08 |
| ATE309212T1 (de) | 2005-11-15 |
| FI942167L (fi) | 1994-07-08 |
| HUT70219A (en) | 1995-09-28 |
| JP2724634B2 (ja) | 1998-03-09 |
| FI108130B (fi) | 2001-11-30 |
| NO941757L (no) | 1994-05-10 |
| WO1994006767A1 (fr) | 1994-03-31 |
| EP0916657B1 (en) | 2005-11-09 |
| EP0627419A1 (en) | 1994-12-07 |
| ES2139670T3 (es) | 2000-02-16 |
| DK0627419T3 (da) | 2000-04-25 |
| DE69333903T2 (de) | 2006-07-27 |
| ES2247657T3 (es) | 2006-03-01 |
| FI107605B (fi) | 2001-09-14 |
| AU4983293A (en) | 1994-04-12 |
| EP0916657A1 (en) | 1999-05-19 |
| FI20001893L (fi) | 2000-08-28 |
| DE69333903D1 (de) | 2005-12-15 |
| EP0627419B1 (en) | 1999-11-24 |
| HU215598B (hu) | 1999-01-28 |
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