CA1235128A - Derives de disubstitution de proline; preparation et utilisation - Google Patents

Derives de disubstitution de proline; preparation et utilisation

Info

Publication number: CA1235128A
Authority: CA; Canada
Prior art keywords: carbon atoms; formula; compound; beta; represent
Prior art date: 1983-01-07
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

Application number

CA000511617A

Other languages

English (en)

Inventor

Rainer Henning

Hansjorg Urbach

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.)

Sanofi Aventis Deutschland GmbH

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.)

1983-01-07

Filing date

1986-06-13

Publication date

1988-04-12

1983-01-07 Priority claimed from DE19833300316 external-priority patent/DE3300316A1/de

1986-06-13 Application filed by Hoechst AG filed Critical Hoechst AG

1986-06-13 Priority to CA000511617A priority Critical patent/CA1235128A/fr

1988-04-12 Application granted granted Critical

1988-04-12 Publication of CA1235128A publication Critical patent/CA1235128A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000003147 proline derivatives Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 50
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 6
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract 12
238000004519 manufacturing process Methods 0.000 claims abstract 3
150000002431 hydrogen Chemical class 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 4
238000003797 solvolysis reaction Methods 0.000 claims description 4
239000000126 substance Substances 0.000 claims 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims 1
102000004190 Enzymes Human genes 0.000 abstract description 2
108090000790 Enzymes Proteins 0.000 abstract description 2
239000003112 inhibitor Substances 0.000 abstract description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
239000000243 solution Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
-1 sodium hydrides Chemical class 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
241000208422 Rhododendron Species 0.000 description 6
239000012071 phase Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910002651 NO3 Inorganic materials 0.000 description 3
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
229920000180 alkyd Polymers 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
125000006413 ring segment Chemical group 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase 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
239000000047 product Substances 0.000 description 2
230000011514 reflex Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
BIPDTXKSTMCGBL-UHFFFAOYSA-N 1-acetyl-4,5-diethylpyrrolidine-2-carbonitrile Chemical compound CCC1CC(C#N)N(C(C)=O)C1CC BIPDTXKSTMCGBL-UHFFFAOYSA-N 0.000 description 1
VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
239000005541 ACE inhibitor Substances 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
241000132092 Aster Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001429719 Daubentonia madagascariensis Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
101100346656 Drosophila melanogaster strat gene Proteins 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
241001508691 Martes zibellina Species 0.000 description 1
230000006181 N-acylation Effects 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
PGYMHKYDSLLPKX-KLXURFKVSA-M [(1r,2r)-2-acetamidocyclopentyl]-chloromercury Chemical compound CC(=O)N[C@@H]1CCC[C@H]1[Hg]Cl PGYMHKYDSLLPKX-KLXURFKVSA-M 0.000 description 1
HGINCPLSRVDWNT-UHFFFAOYSA-N acrylaldehyde Natural products C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
239000004913 cyclooctene Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
150000002730 mercury Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
OSWAUHHXPGUOPH-DJBFQZMMSA-N n-[(1r,2s)-2-(2-chloro-2-cyanoethyl)cyclopentyl]acetamide Chemical compound CC(=O)N[C@@H]1CCC[C@H]1CC(Cl)C#N OSWAUHHXPGUOPH-DJBFQZMMSA-N 0.000 description 1
LAXLJQYGHNDNMZ-UHFFFAOYSA-N n-[2-(2-chloro-2-cyanoethyl)cyclohexyl]acetamide Chemical compound CC(=O)NC1CCCCC1CC(Cl)C#N LAXLJQYGHNDNMZ-UHFFFAOYSA-N 0.000 description 1
101150115538 nero gene Proteins 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002577 pseudohalo group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000006340 racemization Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000563 toxic property Toxicity 0.000 description 1
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000511617A 1983-01-07 1986-06-13 Derives de disubstitution de proline; preparation et utilisation Expired CA1235128A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000511617A CA1235128A (fr)	1983-01-07	1986-06-13	Derives de disubstitution de proline; preparation et utilisation

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DEP3300316.5		1983-01-07
DE19833300316 DE3300316A1 (de)	1983-01-07	1983-01-07	Disubstituierte prolinderivate, verfahren zu ihrer herstellung und ihre verwendung
CA000444858A CA1220213A (fr)	1983-01-07	1984-01-06	Derives de proline bisubstitues, procede de preparation et utilisation
CA000511617A CA1235128A (fr)	1983-01-07	1986-06-13	Derives de disubstitution de proline; preparation et utilisation

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000444858A Division CA1220213A (fr)	1983-01-07	1984-01-06	Derives de proline bisubstitues, procede de preparation et utilisation

Publications (1)

Publication Number	Publication Date
CA1235128A true CA1235128A (fr)	1988-04-12

Family

ID=25670264

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000511617A Expired CA1235128A (fr)	1983-01-07	1986-06-13	Derives de disubstitution de proline; preparation et utilisation

Country Status (1)

Country	Link
CA (1)	CA1235128A (fr)

1986
- 1986-06-13 CA CA000511617A patent/CA1235128A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-04-12	MKEX	Expiry

Publication	Publication Date	Title
CA1220213A (fr)	1987-04-07	Derives de proline bisubstitues, procede de preparation et utilisation
EP0022219B1 (fr)	1984-10-10	Dérivés de 5-oxo et 5-thioxoproline, procédé pour leur préparation et compositions pharmaceutiques les contenant
US4668797A (en)	1987-05-26	Bicyclic aminoacids as intermediates and processes for their preparation
US4154934A (en)	1979-05-15	Mercaptoacylamino derivatives of heterocyclic carboxylic acids
AU2009208107A1 (en)	2009-09-03	A process for resolving, optionally substituted, mandelic acids by salt formation with a chiral base cyclic amide
JP2509465B2 (ja)	1996-06-19	不飽和アミノ酸を含む医薬
JP2876712B2 (ja)	1999-03-31	光学活性ピラノベンゾオキサジアゾール誘導体
EP0719778A1 (fr)	1996-07-03	Sels de diamine de l'acide clavulanique
CA1235128A (fr)	1988-04-12	Derives de disubstitution de proline; preparation et utilisation
HUT70488A (en)	1995-10-30	Condensed quinolyl-dihydropyridine derivatives, pharmaceutical compositions containing them and process for producing the compounds and the pharmaceutical compositions
CZ280543B6 (cs)	1996-02-14	Způsob výroby nových thienopyranových derivátů
US4325886A (en)	1982-04-20	Optical resolution of acylthiopropionic acid
US4734508A (en)	1988-03-29	Process and intermediates for preparing 4-substituted proline derivatives
US4148907A (en)	1979-04-10	Stereoisomers of 1-(1'benzyl-2'pyrryl)-2-di-sec.-butylaminoethanol and pharmaceutical compositions comprising same
CA1042901A (fr)	1978-11-21	D-penicillamine
US4906757A (en)	1990-03-06	Process for the preparation of dextrorotatory 3-(3-pyridyl)-1H,3H-pyrrolo [1,2-c]-7-thiazolecarboxylic acid
HU176871B (en)	1981-05-28	Process for producing 2-amino-oktahydro-oxasolo-square bracket-3,2-a-square bracket closed-pyrrolo-square bracket-2,1-c-square bracket closed-pyrasine derivatives
EP0039804B1 (fr)	1986-08-20	Amides cycliques
KR950001026B1 (ko)	1995-02-07	페니실란산 유도체의 개선된 제조방법
CA1227802A (fr)	1987-10-06	Derives d'amino-acides bicycliques; methodes de preparation; agents qui renferment ces derives et leur utilisation comme intermediaires; methodes de preparation
US4851514A (en)	1989-07-25	Process for preparing a compound useful in preparing ace inhibitors and intermediate produced thereby
IE47075B1 (en)	1983-12-14	N-acylated thiazolidine, thiazane and morpholine carboxylic acids and esters
FI85483C (fi)	1992-04-27	Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara av 1,4:3,6-dianhydrohexitolderivat.
JP2839955B2 (ja)	1998-12-24	クラブラン酸のジアミン塩
SU351369A1 (ru)		Способ получения алкалоидов