SK282272B6 - Deriváty kyseliny glutárovej, spôsob ich prípravy a medziprodukt tohto postupu - Google Patents

Deriváty kyseliny glutárovej, spôsob ich prípravy a medziprodukt tohto postupu Download PDF

Info

Publication number: SK282272B6
Authority: SK; Slovakia
Prior art keywords: formula; compound; salt; substantially pure; alkyl
Prior art date: 1989-11-16

Application number

SK5685-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK568590A3 (en

Inventor

Ian Thompson Barnish

Keith James

Original Assignee

Pfizer Inc.

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.)

1989-11-16

Filing date

1990-11-16

Publication date

2001-12-03

1990-11-16 Application filed by Pfizer Inc. filed Critical Pfizer Inc.

2001-12-03 Publication of SK568590A3 publication Critical patent/SK568590A3/sk

2001-12-03 Publication of SK282272B6 publication Critical patent/SK282272B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000002310 glutaric acid derivatives Chemical class 0.000 title description 2
239000013067 intermediate product Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 68
150000003839 salts Chemical class 0.000 claims abstract description 67
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical class OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims abstract description 15
238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
230000005595 deprotonation Effects 0.000 claims description 5
238000010537 deprotonation reaction Methods 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
238000006213 oxygenation reaction Methods 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
150000001447 alkali salts Chemical class 0.000 claims 3
150000001768 cations Chemical class 0.000 claims 2
239000000543 intermediate Substances 0.000 abstract description 6
230000003276 anti-hypertensive effect Effects 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
239000002585 base Substances 0.000 description 24
239000000243 solution Substances 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 4
RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical class NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
NXLACVVNHYIYJN-KBPBESRZSA-N (1s)-1-phenyl-n-[(1s)-1-phenylethyl]ethanamine Chemical compound C1([C@H](C)N[C@@H](C)C=2C=CC=CC=2)=CC=CC=C1 NXLACVVNHYIYJN-KBPBESRZSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000010779 crude oil Substances 0.000 description 3
229940043279 diisopropylamine Drugs 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
-1 fiimarates Chemical class 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LXDNMJXYSBKADX-JTQLQIEISA-N 1-[(2s)-2-(aminomethyl)-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]cyclopentane-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)[C@H](CN)CC1(C(O)=O)CCCC1 LXDNMJXYSBKADX-JTQLQIEISA-N 0.000 description 2
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 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
NOOYFQLPKUQDNE-UHFFFAOYSA-N 2-(bromomethyl)prop-2-enoic acid Chemical class OC(=O)C(=C)CBr NOOYFQLPKUQDNE-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
150000002668 lysine derivatives Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000005208 trialkylammonium group Chemical group 0.000 description 2
BIQQWYDMMXATOL-UHFFFAOYSA-N 1-(3-amino-2-carboxypropyl)cyclopentane-1-carboxylic acid Chemical class NCC(C(O)=O)CC1(C(O)=O)CCCC1 BIQQWYDMMXATOL-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
XJXONRRJRVVCJK-UHFFFAOYSA-N C(C)OC(C(CC1(CCCC1)C(=O)O)CN)=O Chemical compound C(C)OC(C(CC1(CCCC1)C(=O)O)CN)=O XJXONRRJRVVCJK-UHFFFAOYSA-N 0.000 description 1
RUAYXSIOKJBQST-UHFFFAOYSA-N COC(=O)C(CC1(CCCC1)C(=O)O)CN Chemical compound COC(=O)C(CC1(CCCC1)C(=O)O)CN RUAYXSIOKJBQST-UHFFFAOYSA-N 0.000 description 1
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
MTCMFVTVXAOHNQ-UHFFFAOYSA-N ethyl 2-(bromomethyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)CBr MTCMFVTVXAOHNQ-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
ZMJJCODMIXQWCQ-UHFFFAOYSA-N potassium;di(propan-2-yl)azanide Chemical compound [K+].CC(C)[N-]C(C)C ZMJJCODMIXQWCQ-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
USPANWSKDHOBOZ-UHFFFAOYSA-N tert-butyl 2-(aminomethyl)prop-2-enoate Chemical compound CC(C)(C)OC(=O)C(=C)CN USPANWSKDHOBOZ-UHFFFAOYSA-N 0.000 description 1
RRAYORBDRLQTCX-UHFFFAOYSA-N tert-butyl 3-bromo-2-methylpropanoate Chemical compound BrCC(C)C(=O)OC(C)(C)C RRAYORBDRLQTCX-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (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)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Lubricants (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK5685-90A 1989-11-16 1990-11-16 Deriváty kyseliny glutárovej, spôsob ich prípravy a medziprodukt tohto postupu SK282272B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898925933A GB8925933D0 (en)	1989-11-16	1989-11-16	Glutaric acid derivatives and preparation thereof

Publications (2)

Publication Number	Publication Date
SK568590A3 SK568590A3 (en)	2001-12-03
SK282272B6 true SK282272B6 (sk)	2001-12-03

Family

ID=10666416

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK5685-90A SK282272B6 (sk)	1989-11-16	1990-11-16	Deriváty kyseliny glutárovej, spôsob ich prípravy a medziprodukt tohto postupu

Country Status (29)

Country	Link
US (1)	US5087732A (de)
EP (1)	EP0432898B1 (de)
JP (1)	JPH03176460A (de)
KR (1)	KR940005958B1 (de)
CN (2)	CN1028361C (de)
AT (1)	ATE104270T1 (de)
AU (1)	AU623814B2 (de)
BR (1)	BR9005746A (de)
CA (1)	CA2029785C (de)
CZ (1)	CZ284374B6 (de)
DE (1)	DE69008130T2 (de)
DK (1)	DK0432898T3 (de)
EG (1)	EG19319A (de)
ES (1)	ES2062410T3 (de)
FI (1)	FI107148B (de)
GB (1)	GB8925933D0 (de)
HU (1)	HU207711B (de)
IE (1)	IE63684B1 (de)
IL (1)	IL96299A (de)
MX (1)	MX23335A (de)
MY (1)	MY104782A (de)
NO (1)	NO179072C (de)
NZ (1)	NZ236080A (de)
PH (1)	PH27369A (de)
PL (2)	PL164610B1 (de)
PT (1)	PT95889B (de)
RU (1)	RU2002734C1 (de)
SK (1)	SK282272B6 (de)
ZA (1)	ZA909161B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5208236A (en) *	1992-09-23	1993-05-04	Schering Corporation	N-(acylaminomethyl)glutaryl amino acids and use
FR2890069B1 (fr) *	2005-08-31	2011-03-04	Senn Chemicals Internat	Intermediaires de synthese pour la preparation de b2-aminoacides et leurs procedes de preparation
ES2400484T3 (es) *	2010-04-15	2013-04-10	Indena S.P.A.	Un proceso para la preparación de derivados de isoserina

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2460891C2 (de) *	1974-12-21	1982-09-23	Gödecke AG, 1000 Berlin	1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
KR880007441A (ko) *	1986-12-11	1988-08-27	알렌 제이.스피겔	스피로-치환된 글루타르아미드 이뇨제
GB8820844D0 (en) *	1988-09-05	1988-10-05	Pfizer Ltd	Therapeutic agents

1989
- 1989-11-16 GB GB898925933A patent/GB8925933D0/en active Pending
1990
- 1990-10-26 US US07/604,845 patent/US5087732A/en not_active Expired - Fee Related
- 1990-11-09 IL IL96299A patent/IL96299A/xx active IP Right Grant
- 1990-11-12 EG EG67590A patent/EG19319A/xx active
- 1990-11-13 DE DE69008130T patent/DE69008130T2/de not_active Expired - Fee Related
- 1990-11-13 CA CA002029785A patent/CA2029785C/en not_active Expired - Fee Related
- 1990-11-13 BR BR909005746A patent/BR9005746A/pt not_active Application Discontinuation
- 1990-11-13 EP EP90312347A patent/EP0432898B1/de not_active Expired - Lifetime
- 1990-11-13 DK DK90312347.9T patent/DK0432898T3/da active
- 1990-11-13 AT AT90312347T patent/ATE104270T1/de not_active IP Right Cessation
- 1990-11-13 ES ES90312347T patent/ES2062410T3/es not_active Expired - Lifetime
- 1990-11-14 MX MX2333590A patent/MX23335A/es unknown
- 1990-11-14 PL PL90299211A patent/PL164610B1/pl unknown
- 1990-11-14 PT PT95889A patent/PT95889B/pt not_active IP Right Cessation
- 1990-11-14 NZ NZ236080A patent/NZ236080A/en unknown
- 1990-11-14 PL PL90287759A patent/PL164543B1/pl unknown
- 1990-11-15 NO NO904961A patent/NO179072C/no not_active IP Right Cessation
- 1990-11-15 AU AU66684/90A patent/AU623814B2/en not_active Ceased
- 1990-11-15 FI FI905664A patent/FI107148B/fi not_active IP Right Cessation
- 1990-11-15 RU SU904831690A patent/RU2002734C1/ru active
- 1990-11-15 ZA ZA909161A patent/ZA909161B/xx unknown
- 1990-11-15 IE IE412190A patent/IE63684B1/en not_active IP Right Cessation
- 1990-11-15 KR KR1019900018469A patent/KR940005958B1/ko not_active IP Right Cessation
- 1990-11-16 MY MYPI90002027A patent/MY104782A/en unknown
- 1990-11-16 PH PH41560A patent/PH27369A/en unknown
- 1990-11-16 CZ CS905685A patent/CZ284374B6/cs not_active IP Right Cessation
- 1990-11-16 JP JP2311242A patent/JPH03176460A/ja active Granted
- 1990-11-16 HU HU907179A patent/HU207711B/hu not_active IP Right Cessation
- 1990-11-16 CN CN90109184A patent/CN1028361C/zh not_active Expired - Fee Related
- 1990-11-16 SK SK5685-90A patent/SK282272B6/sk unknown
1994
- 1994-07-07 CN CN94108400A patent/CN1051991C/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IL96299A0 (en)	1991-08-16
DE69008130D1 (de)	1994-05-19
PH27369A (en)	1993-06-21
EP0432898A3 (en)	1991-09-11
CN1051991C (zh)	2000-05-03
ZA909161B (en)	1992-06-24
JPH03176460A (ja)	1991-07-31
EG19319A (en)	1994-09-29
DE69008130T2 (de)	1994-07-21
EP0432898A2 (de)	1991-06-19
FI905664A (fi)	1991-05-17
HUT56536A (en)	1991-09-30
HU907179D0 (en)	1991-05-28
DK0432898T3 (da)	1994-05-16
CN1107135A (zh)	1995-08-23
ES2062410T3 (es)	1994-12-16
NO904961L (no)	1991-05-21
JPH0585538B2 (de)	1993-12-07
CZ284374B6 (cs)	1998-11-11
PT95889A (pt)	1991-09-13
IL96299A (en)	1997-11-20
AU623814B2 (en)	1992-05-21
NO179072C (no)	1996-07-31
CN1051725A (zh)	1991-05-29
FI107148B (fi)	2001-06-15
CZ568590A3 (cs)	1998-08-12
CA2029785C (en)	1995-03-28
FI905664A0 (fi)	1990-11-15
NZ236080A (en)	1992-04-28
NO179072B (no)	1996-04-22
MY104782A (en)	1994-05-31
BR9005746A (pt)	1991-07-30
PL164610B1 (pl)	1994-08-31
EP0432898B1 (de)	1994-04-13
PL164543B1 (pl)	1994-08-31
AU6668490A (en)	1991-05-23
KR940005958B1 (ko)	1994-06-25
CN1028361C (zh)	1995-05-10
SK568590A3 (en)	2001-12-03
IE63684B1 (en)	1995-05-31
ATE104270T1 (de)	1994-04-15
GB8925933D0 (en)	1990-01-04
IE904121A1 (en)	1991-05-22
PL287759A1 (en)	1991-11-04
US5087732A (en)	1992-02-11
KR910009635A (ko)	1991-06-28
HU207711B (en)	1993-05-28
PT95889B (pt)	1997-06-30
CA2029785A1 (en)	1991-05-17
MX23335A (es)	1993-09-01
NO904961D0 (no)	1990-11-15
RU2002734C1 (ru)	1993-11-15

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