FI107605B - Optisesti aktiivinen 2-[1-(4-t-butyylifenyyli)-2-pyrrolidoni-4-yyli]metoksikarbonyylibentsoehapon alfa-fenyylietyyliamidi, välituote ja menetelmä sen valmistamiseksi - Google Patents

Optisesti aktiivinen 2-[1-(4-t-butyylifenyyli)-2-pyrrolidoni-4-yyli]metoksikarbonyylibentsoehapon alfa-fenyylietyyliamidi, välituote ja menetelmä sen valmistamiseksi Download PDF

Info

Publication number: FI107605B
Authority: FI; Finland
Prior art keywords: formula; compound; optically active; butylphenyl; pyrrolidon
Prior art date: 1992-09-11

Application number

FI942167A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI942167A0 (fi

FI942167L (fi

Inventor

Tomoyasu Ohno

Shingo Yano

Kazuo Ogawa

Tetsuhiko Shirasaka

Original Assignee

Taiho Pharmaceutical 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.)

1992-09-11

Filing date

1994-05-10

Publication date

2001-09-14

1994-05-10 Application filed by Taiho Pharmaceutical Co Ltd filed Critical Taiho Pharmaceutical Co Ltd

1994-05-10 Publication of FI942167A0 publication Critical patent/FI942167A0/fi

1994-07-08 Publication of FI942167L publication Critical patent/FI942167L/fi

2001-09-14 Application granted granted Critical

2001-09-14 Publication of FI107605B publication Critical patent/FI107605B/fi

Links

-1 2- [1- (4-t-butylphenyl) -2-pyrrolidon-4-yl] methoxycarbonylbenzoic acid Chemical compound 0.000 title claims description 36
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 74
239000000203 mixture Substances 0.000 claims description 31
238000000034 method Methods 0.000 claims description 11
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
239000012320 chlorinating reagent Substances 0.000 claims description 6
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical group C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 claims description 3
FNJSWIPFHMKRAT-UHFFFAOYSA-N Monomethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(O)=O FNJSWIPFHMKRAT-UHFFFAOYSA-N 0.000 claims description 3
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 16
238000003786 synthesis reaction Methods 0.000 abstract description 16
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 5
125000000217 alkyl group Chemical group 0.000 abstract description 4
235000012000 cholesterol Nutrition 0.000 abstract description 3
125000004432 carbon atom Chemical group C* 0.000 abstract description 2
235000014113 dietary fatty acids Nutrition 0.000 abstract description 2
239000000194 fatty acid Substances 0.000 abstract description 2
229930195729 fatty acid Natural products 0.000 abstract description 2
150000004665 fatty acids Chemical class 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
208000031226 Hyperlipidaemia Diseases 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
238000001308 synthesis method Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 26
239000002904 solvent Substances 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
150000007514 bases Chemical class 0.000 description 14
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
238000000921 elemental analysis Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
JMVIVASFFKKFQK-UHFFFAOYSA-N 1-phenylpyrrolidin-2-one Chemical class O=C1CCCN1C1=CC=CC=C1 JMVIVASFFKKFQK-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000001819 mass spectrum Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000007858 starting material Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
ZPWDKFLAMVCCET-UHFFFAOYSA-N 4-[1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(C2CC(=O)N(C2)C=2C=CC(=CC=2)C(C)(C)C)=C1 ZPWDKFLAMVCCET-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IFSJQWXZIHWZQG-LBPRGKRZSA-N C1(=CC=CC=C1)[C@H](C)NC(C1=C(C=CC=C1)C(=O)OC)=O Chemical compound C1(=CC=CC=C1)[C@H](C)NC(C1=C(C=CC=C1)C(=O)OC)=O IFSJQWXZIHWZQG-LBPRGKRZSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
QEZGRWSAUJTDEZ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperidine-1-carbonyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)C(=O)N1CCCCC1 QEZGRWSAUJTDEZ-UHFFFAOYSA-N 0.000 description 1
ZPWDKFLAMVCCET-HNNXBMFYSA-N 4-[(3R)-1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]-2-methoxybenzoic acid Chemical compound C(C)(C)(C)C1=CC=C(C=C1)N1C(C[C@@H](C1)C1=CC(=C(C(=O)O)C=C1)OC)=O ZPWDKFLAMVCCET-HNNXBMFYSA-N 0.000 description 1
IMYGMSWPECINMA-AWEZNQCLSA-N C(C)(C)(C)C1=CC=C(C=C1)N1C(C[C@@H](C1)C1=C(C(=O)O)C=CC=C1C(=O)OC)=O Chemical compound C(C)(C)(C)C1=CC=C(C=C1)N1C(C[C@@H](C1)C1=C(C(=O)O)C=CC=C1C(=O)OC)=O IMYGMSWPECINMA-AWEZNQCLSA-N 0.000 description 1
241000289659 Erinaceidae Species 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000004136 fatty acid synthesis Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010575 fractional recrystallization Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
CXBRSNZDFNQVGQ-IRLDBZIGSA-N methyl 2-[(3R)-1-(4-tert-butylphenyl)-5-oxopyrrolidin-3-yl]-3-[[(1R)-1-phenylethyl]carbamoyl]benzoate Chemical compound C1(=CC=CC=C1)[C@@H](C)NC(C1=C(C(=CC=C1)C(=O)OC)[C@H]1CC(N(C1)C1=CC=C(C=C1)C(C)(C)C)=O)=O CXBRSNZDFNQVGQ-IRLDBZIGSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 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
231100000820 toxicity test Toxicity 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 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)

FI942167A 1992-09-11 1994-05-10 Optisesti aktiivinen 2-[1-(4-t-butyylifenyyli)-2-pyrrolidoni-4-yyli]metoksikarbonyylibentsoehapon alfa-fenyylietyyliamidi, välituote ja menetelmä sen valmistamiseksi FI107605B (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP24288792		1992-09-11
JP24288792		1992-09-11
JP9301274		1993-09-08
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
FI942167A0 FI942167A0 (fi)	1994-05-10
FI942167L FI942167L (fi)	1994-07-08
FI107605B true FI107605B (fi)	2001-09-14

Family

ID=17095708

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
FI942167A FI107605B (fi)	1992-09-11	1994-05-10	Optisesti aktiivinen 2-[1-(4-t-butyylifenyyli)-2-pyrrolidoni-4-yyli]metoksikarbonyylibentsoehapon alfa-fenyylietyyliamidi, välituote ja menetelmä sen valmistamiseksi
FI20001893A FI108130B (fi)	1992-09-11	2000-08-28	Menetelmä farmaseuttisesti aktiivisen (S)-(+)-4-[1-(4-t-butyylifenyyli)-2-pyrrolidon-4-yyli]metoksibentsoehapon tai sen esterin valmistamiseksi

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
FI20001893A FI108130B (fi)	1992-09-11	2000-08-28	Menetelmä farmaseuttisesti aktiivisen (S)-(+)-4-[1-(4-t-butyylifenyyli)-2-pyrrolidon-4-yyli]metoksibentsoehapon tai sen esterin valmistamiseksi

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)	ES2139670T3 (ja)
FI (2)	FI107605B (ja)
HU (1)	HU215598B (ja)
NO (1)	NO300130B1 (ja)
WO (1)	WO1994006767A1 (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3412829B2 (ja) *	1998-02-24	2003-06-03	大鵬薬品工業株式会社	「Ｌｐ（ａ）低下剤及びアポ蛋白（ａ）産生抑制剤」

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0393607B1 (en) *	1989-04-19	1996-02-21	Otsuka Pharmaceutical Co., Ltd.	Phenylcarboxylic acid derivatives having a hetero ring
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 DK DK93919628T patent/DK0627419T3/da active
- 1993-09-08 DE DE69333903T patent/DE69333903T2/de not_active Expired - Fee Related
- 1993-09-08 CA CA002122705A patent/CA2122705C/en not_active Expired - Fee Related
- 1993-09-08 AT AT93919628T patent/ATE186907T1/de not_active IP Right Cessation
- 1993-09-08 WO PCT/JP1993/001274 patent/WO1994006767A1/ja not_active Ceased
- 1993-09-08 ES ES93919628T patent/ES2139670T3/es not_active Expired - Lifetime
- 1993-09-08 KR KR1019940701558A patent/KR0141657B1/ko not_active Expired - Fee Related
- 1993-09-08 ES ES98203959T patent/ES2247657T3/es not_active Expired - Lifetime
- 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 JP JP6507962A patent/JP2724634B2/ja not_active Expired - Lifetime
- 1993-09-08 DE DE69327092T patent/DE69327092T2/de not_active Expired - Fee Related
- 1993-09-08 AT AT98203959T patent/ATE309212T1/de not_active IP Right Cessation
- 1993-09-08 EP EP98203959A patent/EP0916657B9/en not_active Expired - Lifetime
- 1993-09-08 AU AU49832/93A patent/AU663233B2/en not_active Ceased
- 1993-09-08 US US08/211,950 patent/US5475118A/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
AU4983293A (en)	1994-04-12
HU215598B (hu)	1999-01-28
DE69327092T2 (de)	2000-05-25
FI942167A0 (fi)	1994-05-10
DK0627419T3 (da)	2000-04-25
DE69327092D1 (de)	1999-12-30
CA2122705A1 (en)	1994-03-31
DE69333903D1 (de)	2005-12-15
CA2122705C (en)	1997-11-18
EP0627419B1 (en)	1999-11-24
EP0916657B9 (en)	2006-05-17
KR0141657B1 (ko)	1998-06-01
HU9401470D0 (en)	1994-08-29
EP0916657B1 (en)	2005-11-09
EP0627419A1 (en)	1994-12-07
FI942167L (fi)	1994-07-08
ATE309212T1 (de)	2005-11-15
ATE186907T1 (de)	1999-12-15
NO941757D0 (no)	1994-05-10
NO941757L (no)	1994-05-10
ES2139670T3 (es)	2000-02-16
FI108130B (fi)	2001-11-30
US5475118A (en)	1995-12-12
AU663233B2 (en)	1995-09-28
HUT70219A (en)	1995-09-28
WO1994006767A1 (fr)	1994-03-31
FI20001893L (fi)	2000-08-28
JP2724634B2 (ja)	1998-03-09
ES2247657T3 (es)	2006-03-01
NO300130B1 (no)	1997-04-14
EP0916657A1 (en)	1999-05-19
EP0627419A4 (en)	1995-02-08
DE69333903T2 (de)	2006-07-27

Publication	Publication Date	Title
FI67695B (fi)	1985-01-31	Foerfarande foer framstaellning av 4-hydroxi-2-oxo-1-pyrrolidinalkanamider
EP0452143B1 (en)	1994-10-05	Process for preparing optically active 3-hydroxypyrrolidine derivatives
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FI107605B (fi)	2001-09-14	Optisesti aktiivinen 2-[1-(4-t-butyylifenyyli)-2-pyrrolidoni-4-yyli]metoksikarbonyylibentsoehapon alfa-fenyylietyyliamidi, välituote ja menetelmä sen valmistamiseksi
FI84473C (fi)	1991-12-10	Foerfarande foer framstaellning av oktahydroindolderivat och mellanprodukter av framstaellningen.
BE897000A (fr)	1983-12-09	Nouveaux derives de la 1,4-dihydropyridine,leur preparation et leur utilisation comme medicaments
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JPWO1994006767A1 (ja)	1994-10-06	光学活性を有する１−フェニルピロリドン誘導体及びその製造中間体並びにそれらの製造方法
Wanner et al.	1991	Biomimetic synthesis of quinolizidine alkaloids
US5142066A (en)	1992-08-25	Stereoselective process for the preparation of 2-amino-ethanol derivatives having a central analgesic activity and intermidiates thereof
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KR0127750B1 (ko)	1998-04-01	피톨리돈 유도체의 제조방법
JP2803879B2 (ja)	1998-09-24	ピロリジン誘導体の製法
EP1140841B1 (fr)	2005-08-17	Derives de 3-phenyl-2, 6-dioxopiperidin-3-yl propionamide et leur procede de preparation
WO2002076940A2 (en)	2002-10-03	Process for preparing arylpiperidine carbinol intermediates and derivatives
HUP0104036A2 (hu)	2002-02-28	Aril-piperidin-karbonil-származékok és közbenső termékeik, és eljárás előállításukra
JPH08165282A (ja)	1996-06-25	２−アルキル−４−オキソ−５、６、７、８−テトラヒドロ−シクロヘプトイミダゾ−ルの製造方法
JPH0333700B2 (ja)	1991-05-20
MXPA01006111A (en)	2002-05-09	3-phenyl-2,6-dioxopiperidin-3-yl propionamide derivatives and method for preparing same