CS274502B2 - Method of glutaramide's derivatives' s-enantiomers production - Google Patents

Method of glutaramide's derivatives' s-enantiomers production Download PDF

Info

Publication number: CS274502B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; hydrogen; cleaved; indanyl; give
Prior art date: 1988-05-19

Application number

CS296589A

Other languages

Czech (cs)

English (en)

Other versions

CS296589A2 (en

Inventor

John Ch Dr Danillewicz

Michael T Dr Williams

Original Assignee

Pfizer

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.)

1988-05-19

Filing date

1989-05-17

Publication date

1991-04-11

1989-05-17 Application filed by Pfizer filed Critical Pfizer

1990-09-12 Publication of CS296589A2 publication Critical patent/CS296589A2/cs

1991-04-11 Publication of CS274502B2 publication Critical patent/CS274502B2/cs

Links

238000000034 method Methods 0.000 title claims description 20
RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 title claims description 4
-1 5-indanyl group Chemical group 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000002148 esters Chemical group 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
238000003776 cleavage reaction Methods 0.000 claims description 6
230000007017 scission Effects 0.000 claims description 6
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 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
ACRRMYGNCBLONC-UHFFFAOYSA-N 1-(cyclopentanecarbonylamino)cyclohexane-1-carboxylic acid Chemical compound C1CCCC1C(=O)NC1(C(=O)O)CCCCC1 ACRRMYGNCBLONC-UHFFFAOYSA-N 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
238000005984 hydrogenation reaction Methods 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000000047 product Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
238000004809 thin layer chromatography Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000003756 stirring Methods 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000203 mixture Substances 0.000 description 8
230000003287 optical effect Effects 0.000 description 8
239000003480 eluent Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
150000005690 diesters Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
102000002723 Atrial Natriuretic Factor Human genes 0.000 description 4
101800001288 Atrial natriuretic factor Proteins 0.000 description 4
101800001890 Atrial natriuretic peptide Proteins 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
NSQLIUXCMFBZME-MPVJKSABSA-N carperitide Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)=O)[C@@H](C)CC)C1=CC=CC=C1 NSQLIUXCMFBZME-MPVJKSABSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
102000003729 Neprilysin Human genes 0.000 description 3
108090000028 Neprilysin Proteins 0.000 description 3
230000004071 biological effect Effects 0.000 description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
229960002179 ephedrine Drugs 0.000 description 3
238000001640 fractional crystallisation Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
229960003908 pseudoephedrine Drugs 0.000 description 3
KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
YQRRFIKLPFQWAO-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yloxy)-2,3-dihydro-1h-indene Chemical compound C1CC2=CC=CC=C2C1OC1C2=CC=CC=C2CC1 YQRRFIKLPFQWAO-UHFFFAOYSA-N 0.000 description 2
HYBVWCCIEBYQJZ-ZDUSSCGKSA-N 1-[(2s)-2-(2-methoxyethoxymethyl)-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]cyclopentane-1-carboxylic acid Chemical compound COCCOC[C@@H](C(=O)OC(C)(C)C)CC1(C(O)=O)CCCC1 HYBVWCCIEBYQJZ-ZDUSSCGKSA-N 0.000 description 2
HYBVWCCIEBYQJZ-UHFFFAOYSA-N 1-[2-(2-methoxyethoxymethyl)-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]cyclopentane-1-carboxylic acid Chemical compound COCCOCC(C(=O)OC(C)(C)C)CC1(C(O)=O)CCCC1 HYBVWCCIEBYQJZ-UHFFFAOYSA-N 0.000 description 2
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
206010019280 Heart failures Diseases 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
ZCLSQRQRWNDNLV-UHFFFAOYSA-N acetic acid;dichloromethane;methanol Chemical compound OC.ClCCl.CC(O)=O ZCLSQRQRWNDNLV-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002934 diuretic Substances 0.000 description 2
229940030606 diuretics Drugs 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
JUCGVCVPNPBJIG-IUCAKERBSA-N (1s,2s)-2-amino-1-phenylpropane-1,3-diol Chemical compound OC[C@H](N)[C@@H](O)C1=CC=CC=C1 JUCGVCVPNPBJIG-IUCAKERBSA-N 0.000 description 1
YSJLXCRKVIGFSW-KRWDZBQOSA-N (2S)-2-(2-methoxyethoxymethyl)-3-(1-phenacyloxycarbonylcyclopentyl)propanoic acid Chemical compound C=1C=CC=CC=1C(=O)COC(=O)C1(C[C@@H](COCCOC)C(O)=O)CCCC1 YSJLXCRKVIGFSW-KRWDZBQOSA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
PLMSUUQZBONVAA-JTQLQIEISA-N 1-[(2s)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentane-1-carboxylic acid Chemical compound COCCOC[C@@H](C(O)=O)CC1(C(O)=O)CCCC1 PLMSUUQZBONVAA-JTQLQIEISA-N 0.000 description 1
VELWSNPVIOITEM-SFHVURJKSA-N 1-[(2s)-3-(2,3-dihydro-1h-inden-5-yloxy)-2-(2-methoxyethoxymethyl)-3-oxopropyl]cyclopentane-1-carboxylic acid Chemical compound C([C@@H](COCCOC)C(=O)OC=1C=C2CCCC2=CC=1)C1(C(O)=O)CCCC1 VELWSNPVIOITEM-SFHVURJKSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
YSJLXCRKVIGFSW-UHFFFAOYSA-N 2-(2-methoxyethoxymethyl)-3-(1-phenacyloxycarbonylcyclopentyl)propanoic acid Chemical compound C=1C=CC=CC=1C(=O)COC(=O)C1(CC(COCCOC)C(O)=O)CCCC1 YSJLXCRKVIGFSW-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
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
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
DRNGLYHKYPNTEA-UHFFFAOYSA-N 4-azaniumylcyclohexane-1-carboxylate Chemical compound NC1CCC(C(O)=O)CC1 DRNGLYHKYPNTEA-UHFFFAOYSA-N 0.000 description 1
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125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
WBSHQGSIZJXJDS-LHGWWSMPSA-N COCCOC[C@H](CC1(CCCC1)C(N[C@H](CC1)CC[C@H]1C(OCC1=CC=CC=C1)=O)=O)C(OC1=CC=C(CCC2)C2=C1)=O Chemical compound COCCOC[C@H](CC1(CCCC1)C(N[C@H](CC1)CC[C@H]1C(OCC1=CC=CC=C1)=O)=O)C(OC1=CC=C(CCC2)C2=C1)=O WBSHQGSIZJXJDS-LHGWWSMPSA-N 0.000 description 1
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238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
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208000006673 asthma Diseases 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
VUPFWCRTJAOTKD-UHFFFAOYSA-N benzyl 4-aminocyclohexane-1-carboxylate Chemical compound C1CC(N)CCC1C(=O)OCC1=CC=CC=C1 VUPFWCRTJAOTKD-UHFFFAOYSA-N 0.000 description 1
OVHDZBAFUMEXCX-UHFFFAOYSA-N benzyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1 OVHDZBAFUMEXCX-UHFFFAOYSA-N 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
ACZWIDANLCXHBM-HRCADAONSA-N candoxatrilat Chemical compound N([C@@H]1CC[C@@H](CC1)C(O)=O)C(=O)C1(C[C@@H](COCCOC)C(O)=O)CCCC1 ACZWIDANLCXHBM-HRCADAONSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
RNOJZAYWQCKGRK-UHFFFAOYSA-N diazene hydrochloride Chemical compound Cl.N=N RNOJZAYWQCKGRK-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
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238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
230000004992 fission Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000005844 heterocyclyloxy group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
208000002551 irritable bowel syndrome Diseases 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
201000006370 kidney failure Diseases 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000001452 natriuretic effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000005192 partition Methods 0.000 description 1
239000000813 peptide hormone Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
NLXPUFZRTPZSDZ-UHFFFAOYSA-N phenacyl 1-[3-(2,3-dihydro-1h-inden-5-yloxy)-2-(2-methoxyethoxymethyl)-3-oxopropyl]cyclopentane-1-carboxylate Chemical compound C=1C=C2CCCC2=CC=1OC(=O)C(COCCOC)CC1(C(=O)OCC(=O)C=2C=CC=CC=2)CCCC1 NLXPUFZRTPZSDZ-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
201000009395 primary hyperaldosteronism Diseases 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Detergent Compositions (AREA)
Hydrogenated Pyridines (AREA)
Cosmetics (AREA)

CS296589A 1988-05-19 1989-05-17 Method of glutaramide's derivatives' s-enantiomers production CS274502B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888811873A GB8811873D0 (en)	1988-05-19	1988-05-19	Therapeutic agents

Publications (2)

Publication Number	Publication Date
CS296589A2 CS296589A2 (en)	1990-09-12
CS274502B2 true CS274502B2 (en)	1991-04-11

Family

ID=10637176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS296589A CS274502B2 (en)	1988-05-19	1989-05-17	Method of glutaramide's derivatives' s-enantiomers production

Country Status (29)

Country	Link
EP (1)	EP0342850B1 (no)
JP (1)	JPH072699B2 (no)
KR (1)	KR920000561B1 (no)
CN (1)	CN1015361B (no)
AT (1)	ATE76399T1 (no)
AU (1)	AU602813B2 (no)
CA (1)	CA1331197C (no)
CS (1)	CS274502B2 (no)
DD (1)	DD283772A5 (no)
DE (1)	DE68901582D1 (no)
DK (1)	DK172032B1 (no)
EG (1)	EG19007A (no)
ES (1)	ES2037418T3 (no)
FI (1)	FI93541C (no)
GB (1)	GB8811873D0 (no)
GR (1)	GR3004968T3 (no)
HU (1)	HU205067B (no)
IE (1)	IE60724B1 (no)
IL (1)	IL90267A (no)
MX (1)	MX16067A (no)
MY (1)	MY104735A (no)
NO (1)	NO173647C (no)
NZ (1)	NZ229186A (no)
PH (1)	PH26740A (no)
PL (1)	PL154813B1 (no)
PT (1)	PT90584B (no)
SU (1)	SU1766251A3 (no)
YU (1)	YU47973B (no)
ZA (1)	ZA893696B (no)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8812597D0 (en) *	1988-05-27	1988-06-29	Pfizer Ltd	Therapeutic agents
GB8820844D0 (en) *	1988-09-05	1988-10-05	Pfizer Ltd	Therapeutic agents
GB9000725D0 (en) *	1990-01-12	1990-03-14	Pfizer Ltd	Therapeutic agents
ES2081183T3 (es) *	1993-09-22	1996-02-16	Pfizer Res & Dev	Hidrogenacion.
US7468390B2 (en)	2002-01-17	2008-12-23	Novartis Ag	Methods of treatment and pharmaceutical composition
AR057882A1 (es)	2005-11-09	2007-12-26	Novartis Ag	Compuestos de accion doble de bloqueadores del receptor de angiotensina e inhibidores de endopeptidasa neutra
US8993631B2 (en)	2010-11-16	2015-03-31	Novartis Ag	Method of treating contrast-induced nephropathy
DK2887961T3 (da)	2012-08-24	2021-07-19	Novartis Ag	Nep-inhibitorer til behandling af sygdomme, der er kendetegnet ved atrieforstørrelse eller -remodellering
WO2017033128A1 (en)	2015-08-25	2017-03-02	Novartis Ag	Biphenyl-substitued 4-amino-butyric acid derivatives and their use in the synthesis of nep inhibitors
US20180311241A1 (en)	2015-10-29	2018-11-01	Cadila Healthcare Limited	Pharmaceutical synergistic combination

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR880007441A (ko) *	1986-12-11	1988-08-27	알렌 제이.스피겔	스피로-치환된 글루타르아미드 이뇨제

1988
- 1988-05-19 GB GB888811873A patent/GB8811873D0/en active Pending
1989
- 1989-05-09 ES ES198989304698T patent/ES2037418T3/es not_active Expired - Lifetime
- 1989-05-09 DE DE8989304698T patent/DE68901582D1/de not_active Expired - Lifetime
- 1989-05-09 EP EP89304698A patent/EP0342850B1/en not_active Expired - Lifetime
- 1989-05-09 AT AT89304698T patent/ATE76399T1/de not_active IP Right Cessation
- 1989-05-11 IL IL90267A patent/IL90267A/xx not_active IP Right Cessation
- 1989-05-16 MY MYPI89000654A patent/MY104735A/en unknown
- 1989-05-17 HU HU892460A patent/HU205067B/hu not_active IP Right Cessation
- 1989-05-17 CA CA000599911A patent/CA1331197C/en not_active Expired - Fee Related
- 1989-05-17 PT PT90584A patent/PT90584B/pt not_active IP Right Cessation
- 1989-05-17 CS CS296589A patent/CS274502B2/cs not_active IP Right Cessation
- 1989-05-17 MX MX1606789A patent/MX16067A/es unknown
- 1989-05-17 SU SU4614002A patent/SU1766251A3/ru active
- 1989-05-17 DD DD89328675A patent/DD283772A5/de not_active IP Right Cessation
- 1989-05-17 ZA ZA893696A patent/ZA893696B/xx unknown
- 1989-05-17 PL PL1989279491A patent/PL154813B1/pl unknown
- 1989-05-18 YU YU102289A patent/YU47973B/sh unknown
- 1989-05-18 JP JP1125479A patent/JPH072699B2/ja not_active Expired - Fee Related
- 1989-05-18 AU AU34904/89A patent/AU602813B2/en not_active Ceased
- 1989-05-18 IE IE161389A patent/IE60724B1/en not_active IP Right Cessation
- 1989-05-18 NO NO892002A patent/NO173647C/no not_active IP Right Cessation
- 1989-05-18 FI FI892386A patent/FI93541C/fi not_active IP Right Cessation
- 1989-05-18 DK DK240889A patent/DK172032B1/da not_active IP Right Cessation
- 1989-05-18 NZ NZ229186A patent/NZ229186A/xx unknown
- 1989-05-19 KR KR1019890006691A patent/KR920000561B1/ko not_active Expired
- 1989-05-19 CN CN89103437A patent/CN1015361B/zh not_active Expired
- 1989-05-21 EG EG25089A patent/EG19007A/xx active
- 1989-06-12 PH PH38643A patent/PH26740A/en unknown
1992
- 1992-06-18 GR GR920401302T patent/GR3004968T3/el unknown

Also Published As

Publication number	Publication date
IE60724B1 (en)	1994-08-10
CA1331197C (en)	1994-08-02
GR3004968T3 (no)	1993-04-28
PT90584B (pt)	1994-09-30
CN1015361B (zh)	1992-02-05
IL90267A (en)	1993-08-18
CN1037704A (zh)	1989-12-06
FI93541B (fi)	1995-01-13
JPH072699B2 (ja)	1995-01-18
ZA893696B (en)	1990-12-28
DD283772A5 (de)	1990-10-24
PL279491A1 (en)	1989-11-27
MY104735A (en)	1994-05-31
EG19007A (en)	1994-11-30
PL154813B1 (en)	1991-09-30
DE68901582D1 (de)	1992-06-25
ES2037418T3 (es)	1993-06-16
HU205067B (en)	1992-03-30
ATE76399T1 (de)	1992-06-15
HUT53596A (en)	1990-11-28
NO173647C (no)	1994-01-12
DK240889A (da)	1989-11-20
FI892386A0 (fi)	1989-05-18
PT90584A (pt)	1989-11-30
IE891613L (en)	1989-11-19
KR920000561B1 (ko)	1992-01-16
EP0342850A1 (en)	1989-11-23
NO892002L (no)	1989-11-20
YU47973B (sh)	1996-08-13
DK172032B1 (da)	1997-09-22
NO173647B (no)	1993-10-04
CS296589A2 (en)	1990-09-12
NZ229186A (en)	1990-10-26
SU1766251A3 (ru)	1992-09-30
YU102289A (en)	1991-06-30
EP0342850B1 (en)	1992-05-20
FI892386L (fi)	1989-11-20
NO892002D0 (no)	1989-05-18
GB8811873D0 (en)	1988-06-22
KR900017993A (ko)	1990-12-20
FI93541C (fi)	1995-04-25
AU602813B2 (en)	1990-10-25
PH26740A (en)	1992-09-28
JPH0222256A (ja)	1990-01-25
IL90267A0 (en)	1989-12-15
MX16067A (es)	1993-10-01
AU3490489A (en)	1989-11-23
DK240889D0 (da)	1989-05-18

Publication	Publication Date	Title
JP2883297B2 (ja)	1999-04-19	合成興奮性アミノ酸
US4153803A (en)	1979-05-08	Cholesterol-lowering phenoxyalkanoic acid esters
US4562263A (en)	1985-12-31	Process for producing 3-(3,4-dihydroxyphenyl) serine
CS274502B2 (en)	1991-04-11	Method of glutaramide's derivatives' s-enantiomers production
HU221194B1 (en)	2002-08-28	Ltb4 antagonist benzopyran derivatives, process for producing them, and pharmaceuticals containing them, and the use of them as ltb4 antagonist for medicaments
WO1997014670A1 (en)	1997-04-24	Lignans, a process for their production and pharmaceutical compositions and uses thereof
US4134991A (en)	1979-01-16	Derivatives of 2-(3-phenyl-2-aminopropionyloxy)-acetic acid
JPH02306947A (ja)	1990-12-20	キラルβ―アミノ酸の製造方法
SU910118A3 (ru)	1982-02-28	Способ получени N @ -глюкофуранозид-6-ил-N @ -нитрозомочевины
AU610379B2 (en)	1991-05-16	New heteroarotinoid derivatives, processes for preparing them and pharmaceutical compositions containing them
GB2036744A (en)	1980-07-02	Eburnane derivatives
CH619468A5 (no)	1980-09-30
JP2001521498A (ja)	2001-11-06	Ｏ−（３−アミノ−２−ヒドロキシ−プロピル）−ヒドロキシミック酸ハロゲン化物の製造方法
EP1501516B1 (en)	2006-06-21	A process for the preparation of benazepril hydrochloride
DK167018B1 (da)	1993-08-16	3-furylamino-1-benzazepiner samt fremgangsmaade til fremstillig deraf
EP0385423B1 (de)	1995-02-08	Verfahren zur Herstellung der optischen Isomeren von 1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluormethylphenyl)-1,6-naphthyridin-3-carbonsäure-ethyl-ester und 1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluormethylphenyl)-1,6-naphthyridin-3-carbonsäure- 2-(N-methyl-N-phenylmethylamino)ethyl ester
HU182338B (en)	1983-12-28	Process for producing bis-hydroxybenzyl derivatives and pharmaceutical compositions containing them
SU1179921A3 (ru)	1985-09-15	Способ получени сложных этиловых эфиров 1-метил-или 1,4-диметил-1 @ -пиррол-2-уксусной кислоты
CN115197115A (zh)	2022-10-18	一种手性5-氧代吡咯烷-3-甲酸的制备方法与应用
KR850000569B1 (ko)	1985-04-29	카르니틴의 아실-유도체 제조방법
US2957877A (en)	1960-10-25	New process for the preparation of organic alkaloid-like compounds
SK568590A3 (en)	2001-12-03	Glutaric acid derivatives and method for the preparation thereof, and intermediate product of said method
Brouillette et al.	1993	Preparation of the Racemate and Enantiomers of 3-Hydroxy-5, 5-dimethylhexanoic Acid
CS208145B2 (cs)	1981-08-31	Způsob výroby nových substituovaných benzocykloalkenylkarboxylových kyselin a popřípadě jejich esterů nebo amidů
JPH02149561A (ja)	1990-06-08	新規カテコール誘導体

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2006-01-11	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20050517