CS276833B6 - Functional derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl -4- oxobutanoic acid - Google Patents

Functional derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl -4- oxobutanoic acid Download PDF

Info

Publication number: CS276833B6
Authority: CS; Czechoslovakia
Prior art keywords: methyl; oxobutanoic acid; difluorobiphenylyl; cation; alkyl
Prior art date: 1990-06-18

Application number

CS903027A

Other languages

Czech (cs)

English (en)

Other versions

CS302790A3 (en

Inventor

Miroslav Ing Csc Kuchar

Marie Prom Chem Poppova

Jaroslava Dr Csc Grimova

Eva Dr Maturova

Original Assignee

Vyzk Ustav Farm Biochem Sp

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.)

1990-06-18

Filing date

1990-06-18

Publication date

1992-08-12

1990-06-18 Application filed by Vyzk Ustav Farm Biochem Sp filed Critical Vyzk Ustav Farm Biochem Sp

1990-06-18 Priority to CS903027A priority Critical patent/CS276833B6/cs

1991-06-17 Priority to US07/716,814 priority patent/US5177204A/en

1991-06-18 Priority to EP91109980A priority patent/EP0465879B1/de

1991-06-18 Priority to DE69114927T priority patent/DE69114927T2/de

1991-06-18 Priority to CA002044837A priority patent/CA2044837A1/en

1991-06-18 Priority to JP3146257A priority patent/JPH04253936A/ja

1991-06-18 Priority to AT91109980T priority patent/ATE130838T1/de

1992-03-18 Publication of CS302790A3 publication Critical patent/CS302790A3/cs

1992-08-12 Publication of CS276833B6 publication Critical patent/CS276833B6/cs

Links

BJPZBSNQSTVMIT-UHFFFAOYSA-N 4-(2,6-difluoro-3-phenylphenyl)-2-methyl-4-oxobutanoic acid Chemical class OC(=O)C(C)CC(=O)C1=C(F)C=CC(C=2C=CC=CC=2)=C1F BJPZBSNQSTVMIT-UHFFFAOYSA-N 0.000 title claims abstract description 10
-1 cyclohexylamine cation Chemical class 0.000 claims abstract description 14
PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
239000004472 Lysine Substances 0.000 claims abstract description 5
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 4
150000007529 inorganic bases Chemical class 0.000 claims abstract description 4
150000007530 organic bases Chemical class 0.000 claims abstract description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
239000000126 substance Substances 0.000 abstract description 8
230000003110 anti-inflammatory effect Effects 0.000 abstract description 7
125000000217 alkyl group Chemical group 0.000 abstract description 6
239000002253 acid Substances 0.000 abstract description 4
125000004432 carbon atom Chemical group C* 0.000 abstract description 4
230000001225 therapeutic effect Effects 0.000 abstract description 4
150000001768 cations Chemical class 0.000 abstract 2
239000002184 metal Substances 0.000 abstract 1
238000012986 modification Methods 0.000 abstract 1
230000004048 modification Effects 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
229910052799 carbon Inorganic materials 0.000 description 15
239000000203 mixture Substances 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
235000018977 lysine Nutrition 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
235000019766 L-Lysine Nutrition 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000036983 biotransformation Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
FYPVXEILSNEKOO-UHFFFAOYSA-L calcium;butanoate Chemical compound [Ca+2].CCCC([O-])=O.CCCC([O-])=O FYPVXEILSNEKOO-UHFFFAOYSA-L 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000003946 cyclohexylamines Chemical class 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000000034 method Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
125000005322 morpholin-1-yl group Chemical group 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 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
238000001556 precipitation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001562 ulcerogenic effect Effects 0.000 description 1
238000005292 vacuum distillation 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
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
- 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
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

CS903027A 1990-06-18 1990-06-18 Functional derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl -4- oxobutanoic acid CS276833B6 (en)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
CS903027A CS276833B6 (en)	1990-06-18	1990-06-18	Functional derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl -4- oxobutanoic acid
US07/716,814 US5177204A (en)	1990-06-18	1991-06-17	Derivatives of 4-(2,4-difluorbiphenylyl)-2-methyl-4-oxobutanoic acid
EP91109980A EP0465879B1 (de)	1990-06-18	1991-06-18	Derivate der 4-(2,4-Difluorbiphenyl)-2-methyl-4-oxobutansäure
DE69114927T DE69114927T2 (de)	1990-06-18	1991-06-18	Derivate der 4-(2,4-Difluorbiphenyl)-2-methyl-4-oxobutansäure.
CA002044837A CA2044837A1 (en)	1990-06-18	1991-06-18	Derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl-4-oxobutanoic acid
JP3146257A JPH04253936A (ja)	1990-06-18	1991-06-18	４−（２，４−ジフルオロビィフェニリル）−２−メチル−４−オキソブタン酸誘導体［４−（２，４−ｄｉｆｌｕｏｒｂｉｐｈｅｎｙｌｙｌ）−２−ｍｅｔｈｙｌ−４−ｏｘｏｂｕｔａｎｏｉｃ　ａｃｉｄ］およびその塩類
AT91109980T ATE130838T1 (de)	1990-06-18	1991-06-18	Derivate der 4-(2,4-difluorbiphenyl)-2-methyl-4- oxobutansäure.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS903027A CS276833B6 (en)	1990-06-18	1990-06-18	Functional derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl -4- oxobutanoic acid

Publications (2)

Publication Number	Publication Date
CS302790A3 CS302790A3 (en)	1992-03-18
CS276833B6 true CS276833B6 (en)	1992-08-12

Family

ID=5369145

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS903027A CS276833B6 (en)	1990-06-18	1990-06-18	Functional derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl -4- oxobutanoic acid

Country Status (7)

Country	Link
US (1)	US5177204A (de)
EP (1)	EP0465879B1 (de)
JP (1)	JPH04253936A (de)
AT (1)	ATE130838T1 (de)
CA (1)	CA2044837A1 (de)
CS (1)	CS276833B6 (de)
DE (1)	DE69114927T2 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL115995A0 (en) *	1994-11-15	1996-01-31	Bayer Ag	Substituted 4-biarylbutyric or 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors
US5789434A (en) *	1994-11-15	1998-08-04	Bayer Corporation	Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors
US5886022A (en) *	1995-06-05	1999-03-23	Bayer Corporation	Substituted cycloalkanecarboxylic acid derivatives as matrix metalloprotease inhibitors
EP1031349A1 (de) *	1999-02-25	2000-08-30	Bayer Aktiengesellschaft	Verwendung von substituierten 4-Biarylbuttersäuren und 5-Biarylpentansäuren zur Behandlung von zerebralen Krankheiten
KR100405914B1 (ko) *	2000-04-25	2003-11-15	삼성전자주식회사	메트릭스 메탈로프로테이나제의 저해제로서의 비페닐부티릭산 유도체
KR100405913B1 (ko) *	2000-04-25	2003-11-14	삼성전자주식회사	메트릭스 메탈로프로테이나제의 저해제로서의 비페닐부티릭산 유도체

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CS243570B1 (en) *	1984-08-31	1986-06-12	Miroslav Kuchar	Omega-aryloxoalkane acids

1990
- 1990-06-18 CS CS903027A patent/CS276833B6/cs unknown
1991
- 1991-06-17 US US07/716,814 patent/US5177204A/en not_active Expired - Fee Related
- 1991-06-18 AT AT91109980T patent/ATE130838T1/de not_active IP Right Cessation
- 1991-06-18 EP EP91109980A patent/EP0465879B1/de not_active Expired - Lifetime
- 1991-06-18 JP JP3146257A patent/JPH04253936A/ja active Pending
- 1991-06-18 DE DE69114927T patent/DE69114927T2/de not_active Expired - Fee Related
- 1991-06-18 CA CA002044837A patent/CA2044837A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CA2044837A1 (en)	1991-12-19
EP0465879A1 (de)	1992-01-15
EP0465879B1 (de)	1995-11-29
CS302790A3 (en)	1992-03-18
DE69114927T2 (de)	1996-04-18
DE69114927D1 (de)	1996-01-11
ATE130838T1 (de)	1995-12-15
US5177204A (en)	1993-01-05
JPH04253936A (ja)	1992-09-09

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IE56343B1 (en)	1991-07-03	Anti-inflammatory products derived from methylene-diphosphonic acid,and process for their preparation
FI77227B (fi)	1988-10-31	Foerfarande foer framstaellning farmakologiskt aktiva 1-metyl-5-p-toluoylpyrrol-2-aettiksyra amider.
CS276833B6 (en)	1992-08-12	Functional derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl -4- oxobutanoic acid
EP0561846A1 (de)	1993-09-29	4,5-dihydroxy und 4,5,8-trihydroxy-9,10-dioxo-2-anthracencarbonsäure-dikohlensäureester und urethane mit therapeutischer wirkung.
EP0051514B1 (de)	1983-11-23	Cinnamoyl-Zimtsäure-Derivat, seine Herstellung und seine therapeutische Anwendung
JPS58194873A (ja)	1983-11-12	１−（３，４，５−トリメトキシシンナモイル）−４−アミノカルボニルメチル置換ピペラジン誘導体
KR100221767B1 (ko)	1999-09-15	[1s-(1r,2s,3r*)]-n-(4-모르폴리닐술포닐)-l-페닐알라닐-3-(2-아미노-4-티아졸릴)-n-[(1-시클로헥실메틸)-2,3-디히드록시-5-메틸헥실]-l-알라닌아미드의 개선된 제조 방법
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HU223476B1 (hu)	2004-07-28	Új intermedierek tiolok előállításához
US2557284A (en)	1951-06-19	Esters of pantothenic acid, intermediates thereof, and process for their production
SK94793A3 (en)	1994-03-09	N-[[4,5-dihydroxy-and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo- -2-anthracene-yl] carbonyl] amino acids useful in the therapy of osteorticular affections
US3715382A (en)	1973-02-06	N-ACYL- alpha -HYDRAZINO- beta -(PHENYL) PROPIONITRILES
HU180209B (en)	1983-02-28	Process for producing substituted acyl-bracket-bicyclic aryl-bracket closed-amino alkanoic acids
JPH0377179B2 (de)	1991-12-09
US3453315A (en)	1969-07-01	9-isopropylidenyl-9,10-dihydro-anthracene-10-carboxylic acid esters
US4055580A (en)	1977-10-25	Derivatives of aminomethylcyclohexanecarboxylic acid
FI96417B (fi)	1996-03-15	Menetelmä uusien terapeuttisesti käyttökelpoisten isokinoliinijohdannaisten valmistamiseksi
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