SU1327787A3 - Способ получени цис,эндо-2-азабицикло-/3,3,0/-октан-3-карбоновых кислот или их кислотно-аддитивных солей - Google Patents

Способ получени цис,эндо-2-азабицикло-/3,3,0/-октан-3-карбоновых кислот или их кислотно-аддитивных солей Download PDF

Info

Publication number: SU1327787A3
Authority: SU; USSR - Soviet Union
Prior art keywords: octane; endo; azabicyclo; carboxylic acid; cis
Prior art date: 1981-11-05

Application number

SU823513217A

Other languages

English (en)

Russian (ru)

Inventor

Теетц Фолькер

Гайгер Рольф

Урбах Хансйорг

Беккер Райнхард

Шелькенс Бернвард

Original Assignee

Хехст Аг (Фирма)

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.)

1981-11-05

Filing date

1982-11-03

Publication date

1987-07-30

1982-11-03 Application filed by Хехст Аг (Фирма) filed Critical Хехст Аг (Фирма)

1987-07-30 Application granted granted Critical

1987-07-30 Publication of SU1327787A3 publication Critical patent/SU1327787A3/ru

1993-05-07 Priority to LV930305A priority Critical patent/LV5255A3/xx

1993-06-12 Priority to LTRP654A priority patent/LT2582B/xx

Links

238000000034 method Methods 0.000 title description 4
150000003839 salts Chemical class 0.000 title description 2
239000000654 additive Substances 0.000 title 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 29
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
150000001875 compounds Chemical class 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
-1 ethoxy-3-phenyl-propyl Chemical group 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000002253 acid Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
239000004472 Lysine Substances 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229960003237 betaine Drugs 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
150000003751 zinc Chemical class 0.000 description 4
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000003245 coal Substances 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
235000004279 alanine Nutrition 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
230000001603 reducing effect Effects 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
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 description 1
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
101800000734 Angiotensin-1 Proteins 0.000 description 1
102400000344 Angiotensin-1 Human genes 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OCYXHBFFEFDYSJ-UHFFFAOYSA-N C(O)(O)=O.C(C)[Na] Chemical compound C(O)(O)=O.C(C)[Na] OCYXHBFFEFDYSJ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241001481789 Rupicapra Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001294 alanine derivatives Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
LJYCJYJAOWYANE-UHFFFAOYSA-N ethyl 2-benzoylprop-2-enoate Chemical compound CCOC(=O)C(=C)C(=O)C1=CC=CC=C1 LJYCJYJAOWYANE-UHFFFAOYSA-N 0.000 description 1
FVLGPYFFONYLRZ-UHFFFAOYSA-N ethyl 2-benzylprop-2-enoate Chemical compound CCOC(=O)C(=C)CC1=CC=CC=C1 FVLGPYFFONYLRZ-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 1

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Peptides Or Proteins (AREA)
Indole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU823513217A 1981-11-05 1982-11-03 Способ получени цис,эндо-2-азабицикло-/3,3,0/-октан-3-карбоновых кислот или их кислотно-аддитивных солей SU1327787A3 (ru)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
LV930305A LV5255A3 (lv)	1981-11-05	1993-05-07	Panemiens cis endo-2-aza-biciklo-(3,3,0)-oktan-3-karbonskabju un to aditivo saju ar skabem iegusanai
LTRP654A LT2582B (lt)	1981-11-05	1993-06-12	Endo-2-azabiciklo-(3,3,0)-oktan-3-karboniniu rugsciu ir ju drusku gavimo budas

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3143946		1981-11-05

Publications (1)

Publication Number	Publication Date
SU1327787A3 true SU1327787A3 (ru)	1987-07-30

Family

ID=6145696

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU823513217A SU1327787A3 (ru)	1981-11-05	1982-11-03	Способ получени цис,эндо-2-азабицикло-/3,3,0/-октан-3-карбоновых кислот или их кислотно-аддитивных солей

Country Status (4)

Country	Link
JP (3)	JPS58103364A (hu)
MX (1)	MX9217A (hu)
SU (1)	SU1327787A3 (hu)
ZA (1)	ZA828085B (hu)

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DE3324263A1 (de) *	1983-07-06	1985-01-17	Hoechst Ag, 6230 Frankfurt	Derivate der 2-azabicyclo(3.1.0)hexan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie 2-azabicyclo(3.1.0)hexan-derivate als zwischenprodukte und verfahren zu deren herstellung
DE3333455A1 (de) *	1983-09-16	1985-04-11	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung n-alkylierter dipeptide und deren estern
DE3413710A1 (de) *	1984-04-12	1985-10-24	Hoechst Ag, 6230 Frankfurt	Verfahren zur behandlung der herzinsuffizienz
US4925969A (en) *	1985-02-04	1990-05-15	Kanegafuchi Kagaku Kogyo Kabushiki Kaisha	Process for preparing ethyl-alpha-amino-gamma-oxo-gamma-phenybutyrate derivatives
DE3536687A1 (de) *	1985-10-15	1987-04-16	Hoechst Ag	Verfahren zur behandlung von atherosklerose, thrombose und der peripheren gefaesskrankheit
DE3633496A1 (de) *	1986-10-02	1988-04-14	Hoechst Ag	Kombination von angiotensin-converting-enzyme-hemmern mit calciumantagonisten sowie deren verwendung in arzneimitteln
JP2754010B2 (ja) *	1988-05-23	1998-05-20	株式会社リコー	画像形成装置に於ける像担持体のクリーニング方法
US4947750A (en) *	1988-08-19	1990-08-14	Presstek, Inc.	Printing member for a press with dampening
JP3316639B2 (ja) *	1993-03-05	2002-08-19	コニカ株式会社	高感度で安定性の優れたハロゲン化銀写真感光材料
JP3792777B2 (ja) *	1996-05-10	2006-07-05	株式会社カネカ	１−アルコキシカルボニル−３−フェニルプロピル誘導体の製造方法
AR033048A1 (es)	2001-03-19	2003-12-03	Kaneka Corp	Metodo para la purificacion de la n-(1(s)-etoxicarbonil-3-fenilpropil) -l-alanina
US7732620B2 (en) *	2004-01-19	2010-06-08	Lupin Limited	Process for crystallization of Ramipril and preparation of a hydrated form thereof

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Publication number	Priority date	Publication date	Assignee	Title
FR2503155A2 (fr) *	1980-10-02	1982-10-08	Science Union & Cie	Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme
DE3177311D1 (de) *	1980-08-30	1994-06-09	Hoechst Ag	Aminosäurederivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung.
ZA817261B (en) *	1980-10-23	1982-09-29	Schering Corp	Carboxyalkyl dipeptides,processes for their production and pharmaceutical compositions containing them
JPH074338B2 (ja) *	1987-02-27	1995-01-25	オリンパス光学工業株式会社	内視鏡

1982
- 1982-11-03 SU SU823513217A patent/SU1327787A3/ru active
- 1982-11-04 ZA ZA828085A patent/ZA828085B/xx unknown
- 1982-11-04 JP JP19262282A patent/JPS58103364A/ja active Granted
1986
- 1986-04-21 JP JP9018886A patent/JPS61293967A/ja active Granted
- 1986-04-21 JP JP61090187A patent/JPS6251A/ja active Granted
1989
- 1989-01-05 MX MX921789A patent/MX9217A/es unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Выложенла за вка 2703828, кл. С 07 D 207/16, 1977. Европейский патент № 0012401, кл. С 07 С 103/52, 1980. *

Also Published As

Publication number	Publication date
MX9217A (es)	1993-07-01
JPH047741B2 (hu)	1992-02-12
ZA828085B (en)	1983-09-28
JPS6251A (ja)	1987-01-06
JPS58103364A (ja)	1983-06-20
JPH0531544B2 (hu)	1993-05-12
JPS61293967A (ja)	1986-12-24
JPH0559105B2 (hu)	1993-08-30

Publication	Publication Date	Title
CA1198118A (en)	1985-12-17	Derivatives of cycloalka[c]pyrrolcarboxylic acids, a process for their preparation, agents containing these compounds, and their use, and new cycloalka[c]pyrrolcarboxylic acidsas intermediates, and a process for their preparation
SU1327787A3 (ru)	1987-07-30	Способ получени цис,эндо-2-азабицикло-/3,3,0/-октан-3-карбоновых кислот или их кислотно-аддитивных солей
JPH0694443B2 (ja)	1994-11-24	アミノ酸誘導体
SU1320207A1 (ru)	1987-06-30	Правовращающий энантиомер ( @ )- @ -этил-2-оксо-1-пирролидинацетамид,обладающий мнезической активностью
JPS6059226B2 (ja)	1985-12-24	プロリン誘導体および関連化合物
JPS59118766A (ja)	1984-07-09	シス，エンド−２−アザビシクロ〔５．３．０〕デカン−３−カルボン酸の誘導体およびその製法
JPH0472839B2 (hu)	1992-11-19
NO863944L (no)	1986-12-01	L-dopa-derivater, fremgangsmaate til deres fremstilling og farmasoeytisk blanding inneholdende disse derivater.
Herz et al.	1948	Alkylation of Substituted Malonic and Cyanoacetic Esters with 2-Diamethylaminomethylpyrrole. A Proposed Synthesis of β-2-Pyrrolealanine1
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