CA1310972C - Derives d'acide amines bicycliques, procede pour leur preparation, agents en contenant et leur utilisation - Google Patents

Derives d'acide amines bicycliques, procede pour leur preparation, agents en contenant et leur utilisation

Info

Publication number: CA1310972C
Authority: CA; Canada
Prior art keywords: iii; formula; compounds; acid; tert
Prior art date: 1985-05-23
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

CA000615802A

Other languages

English (en)

Inventor

Hansjorg Urbach

Rainer Henning

Reinhard Becker

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1985-05-23

Filing date

1990-07-26

Publication date

1992-12-01

1985-05-23 Priority claimed from DE19853518514 external-priority patent/DE3518514A1/de

1990-07-26 Application filed by Hoechst AG filed Critical Hoechst AG

1992-12-01 Application granted granted Critical

1992-12-01 Publication of CA1310972C publication Critical patent/CA1310972C/fr

2006-05-22 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 25
238000002360 preparation method Methods 0.000 title claims abstract description 10
230000008569 process Effects 0.000 title claims abstract description 10
-1 of bicyclic amino acids Chemical class 0.000 title abstract description 19
239000003795 chemical substances by application Substances 0.000 title description 4
239000002253 acid Substances 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
229910052799 carbon Inorganic materials 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 71
238000006243 chemical reaction Methods 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
238000005903 acid hydrolysis reaction Methods 0.000 claims 1
238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
125000002560 nitrile group Chemical group 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 14
235000013350 formula milk Nutrition 0.000 description 61
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
239000000243 solution Substances 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
238000005160 1H NMR spectroscopy Methods 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
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229910052717 sulfur Inorganic materials 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
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230000015572 biosynthetic process Effects 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
229940073584 methylene chloride Drugs 0.000 description 5
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239000000741 silica gel Substances 0.000 description 5
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239000002904 solvent Substances 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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229910052681 coesite Inorganic materials 0.000 description 4
229910052906 cristobalite Inorganic materials 0.000 description 4
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
229910052682 stishovite Inorganic materials 0.000 description 4
229910052905 tridymite Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
125000006413 ring segment Chemical group 0.000 description 3
238000006884 silylation reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
101100346656 Drosophila melanogaster strat gene Proteins 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
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XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
229960003767 alanine Drugs 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
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239000003480 eluent Substances 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
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238000001990 intravenous administration Methods 0.000 description 2
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125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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244000215068 Acacia senegal Species 0.000 description 1
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208000021822 hypotensive Diseases 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
PAQZWJGSJMLPMG-UHFFFAOYSA-N propylphosphonic anhydride Substances CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229940071138 stearyl fumarate Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000563 toxic property Toxicity 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA000615802A 1985-05-23 1990-07-26 Derives d'acide amines bicycliques, procede pour leur preparation, agents en contenant et leur utilisation Expired - Lifetime CA1310972C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19853518514 DE3518514A1 (de)	1985-05-23	1985-05-23	Neue derivate bicyclischer aminosaeuren, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung
DEP3518514.7		1985-05-23
CA000509785A CA1310794C (fr)	1985-05-23	1986-05-22	Derives d'acides amines bicycliques, procede pour leur preparation, agents en contenant et leur utilisation

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000509785A Division CA1310794C (fr)	1985-05-23	1986-05-22	Derives d'acides amines bicycliques, procede pour leur preparation, agents en contenant et leur utilisation

Publications (1)

Publication Number	Publication Date
CA1310972C true CA1310972C (fr)	1992-12-01

Family

ID=25671006

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000615802A Expired - Lifetime CA1310972C (fr)	1985-05-23	1990-07-26	Derives d'acide amines bicycliques, procede pour leur preparation, agents en contenant et leur utilisation

Country Status (1)

Country	Link
CA (1)	CA1310972C (fr)

1990
- 1990-07-26 CA CA000615802A patent/CA1310972C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2009-12-01	MKEX	Expiry

Publication	Publication Date	Title
CA1275349C (fr)	1990-10-16	Derives d'acide aminique
US4714708A (en)	1987-12-22	Derivatives of cis, endo-2-azabicyclo[5.3.0]decane-3-carboxylic acid, and their use for treating hypertension
US5053519A (en)	1991-10-01	Cis, endo-2-azabicyclo-[3.3.0]-octane-5-carboxylic acids
US4591598A (en)	1986-05-27	Derivatives of 2-azabicyclo[3.1.0]hexane-3-carboxylic acid, and hypotensive use thereof
US4562202A (en)	1985-12-31	N-Acyl hexahydroindole-2-carboxylic acids and anti-hypertensive use thereof
US4614805A (en)	1986-09-30	Bicyclic amino acids as intermediates in the preparation of tricyclic amino acids and processes for their preparation
WO1989007610A1 (fr)	1989-08-24	INHIBITEUR DE RENINE CONTENANT DES AMINOACIDES AVEC UN HETEROATOME alpha
US4620012A (en)	1986-10-28	Spirocyclic aminoacid derivatives, processes for their preparation, agents containing them and their use and new spirocyclic aminoacids as intermediates and processes for their preparation
NZ229281A (en)	1991-11-26	Diol-containing renin inhibitors
EP0049658A1 (fr)	1982-04-14	Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant
GB2086393A (en)	1982-05-12	Bicyclic compounds
WO2005054194A1 (fr)	2005-06-16	Procede de preparation de (2s, 3ar, 7as)-octahydro-1h-indole-2-acide carboxylique en tant qu'intermediaire dans la preparation de trandolapril par reaction d'un cyclohexyl aziridine avec un dialkyl malonate
EP0061684A1 (fr)	1982-10-06	Composés d'urée comme agents antihypertensifs
EP0065301A1 (fr)	1982-11-24	Dérivés des acides isoquinoléine-carboxyliques, leur procédé de préparation et compositions pharmaceutiques qui les contiennent
KR910001438B1 (ko)	1991-03-07	광학적 활성 비시클릭 이미노-α-카복실산 에스테르 라세미체의 분할방법
US4920144A (en)	1990-04-24	Derivatives of bicyclic amino acids, agents containing them and their use as hypotensives
CA1310972C (fr)	1992-12-01	Derives d'acide amines bicycliques, procede pour leur preparation, agents en contenant et leur utilisation
US5175306A (en)	1992-12-29	Process for the resolution of racemates of optically active bicyclic imino-α-carboxylic esters
JPH0379339B2 (fr)	1991-12-18