CS199693B2 - Způsob výroby derivátů thiazolidin-, thiazana morfolinkarboxylových kyselin - Google Patents

Způsob výroby derivátů thiazolidin-, thiazana morfolinkarboxylových kyselin Download PDF

Info

Publication number: CS199693B2
Authority: CS; Czechoslovakia
Prior art keywords: acid; ethyl acetate; formula; salt; carbon atoms
Prior art date: 1976-12-03

Application number

CS777853A

Other languages

Czech (cs)

English (en)

Inventor

Miguel A Ondetti

Original Assignee

Squibb & Sons 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.)

1976-12-03

Filing date

1977-11-28

Publication date

1980-07-31

1977-11-28 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1980-07-31 Publication of CS199693B2 publication Critical patent/CS199693B2/cs

Links

OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 title claims description 4
STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical class OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title 1
150000003839 salts Chemical group 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
229910052717 sulfur Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
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 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
-1 haloacyl halide Chemical class 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 9
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 0.000 description 3
IHBVNSPHKMCPST-UHFFFAOYSA-N 3-bromopropanoyl chloride Chemical compound ClC(=O)CCBr IHBVNSPHKMCPST-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
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238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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239000007858 starting material Substances 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
UNUDUTMFKRKUIJ-UHFFFAOYSA-N 4-oxopentanethioyl chloride Chemical compound CC(=O)CCC(Cl)=S UNUDUTMFKRKUIJ-UHFFFAOYSA-N 0.000 description 2
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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230000015572 biosynthetic process Effects 0.000 description 2
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239000010949 copper Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
150000002500 ions Chemical class 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
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
JUNOWSHJELIDQP-UHFFFAOYSA-N morpholin-4-ium-3-carboxylate Chemical compound OC(=O)C1COCCN1 JUNOWSHJELIDQP-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000013014 purified material Substances 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
LUDPWTHDXSOXDX-UHFFFAOYSA-N s-(3-chloro-2-methyl-3-oxopropyl) ethanethioate Chemical compound ClC(=O)C(C)CSC(C)=O LUDPWTHDXSOXDX-UHFFFAOYSA-N 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
238000005245 sintering Methods 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 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
AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical compound C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 description 1
ULSZVNJBVJWEJE-UHFFFAOYSA-N thiazolidine-2-carboxylic acid Chemical compound OC(=O)C1NCCS1 ULSZVNJBVJWEJE-UHFFFAOYSA-N 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000011345 viscous material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

CS777853A 1976-12-03 1977-11-28 Způsob výroby derivátů thiazolidin-, thiazana morfolinkarboxylových kyselin CS199693B2 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US74728176A	1976-12-03	1976-12-03

Publications (1)

Publication Number	Publication Date
CS199693B2 true CS199693B2 (cs)	1980-07-31

Family

ID=25004426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS777853A CS199693B2 (cs)	1976-12-03	1977-11-28	Způsob výroby derivátů thiazolidin-, thiazana morfolinkarboxylových kyselin

Country Status (5)

Country	Link
BE (1)	BE861454A (fr)
CS (1)	CS199693B2 (fr)
HU (1)	HU175671B (fr)
SU (2)	SU786895A3 (fr)
ZA (1)	ZA777062B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4220791A (en)	1979-03-08	1980-09-02	E. R. Squibb & Sons, Inc.	Mercaptoacylpyrazolidinone carboxylic acid derivatives
US4211786A (en) *	1979-03-08	1980-07-08	E. R. Squibb & Sons, Inc.	Mercaptoacyldihydropyrazole carboxylic acid derivatives
US4221804A (en) *	1979-09-27	1980-09-09	Rovnyak George C	Mercaptoacyldihydropyrazole carboxylic acid derivatives
US4254267A (en)	1979-10-25	1981-03-03	E. R. Squibb & Sons, Inc.	Mercaptoacyldihydropyrazole carboxylic acid derivatives
US4308392A (en)	1979-12-03	1981-12-29	E. R. Squibb & Sons, Inc.	Hydroxamic acid derivatives of mercaptoacyl amino acids
US4284561A (en)	1979-12-03	1981-08-18	E. R. Squibb & Sons, Inc.	Hydroxamic acid derivatives of mercaptoacyl amino acids
US4321392A (en) *	1980-02-06	1982-03-23	E. R. Squibb & Sons, Inc.	Mercaptoacyl derivatives of 4-oxazolidine-carboxylic acids
US4482725A (en) *	1980-04-03	1984-11-13	E. R. Squibb & Sons, Inc.	S-Acylation products of mercaptoacyl amino acids and carboxyl group containing diuretics

1977
- 1977-11-28 ZA ZA00777062A patent/ZA777062B/xx unknown
- 1977-11-28 CS CS777853A patent/CS199693B2/cs unknown
- 1977-12-01 HU HU77SU960A patent/HU175671B/hu not_active IP Right Cessation
- 1977-12-02 BE BE183133A patent/BE861454A/fr not_active IP Right Cessation
- 1977-12-02 SU SU772548901A patent/SU786895A3/ru active
1979
- 1979-02-06 SU SU792719249A patent/SU795470A3/ru active

Also Published As

Publication number	Publication date
ZA777062B (en)	1979-02-28
SU795470A3 (ru)	1981-01-07
SU786895A3 (ru)	1980-12-07
HU175671B (hu)	1980-09-28
BE861454A (fr)	1978-06-02

Publication	Publication Date	Title
US4192878A (en)	1980-03-11	Derivatives of thiazolidinecarboxylic acids and related acids
US4108886A (en)	1978-08-22	Thiopropanoylamino acid derivatives
FI68221C (fi)	1985-08-12	Foerfarande foer framstaellning av terapeutiskt anvaendbara deivat av prolin och pipekolinsyra
US4129566A (en)	1978-12-12	Derivatives of dehydrocyclicimino acids
US4046889A (en)	1977-09-06	Azetidine-2-carboxylic acid derivatives
US4154934A (en)	1979-05-15	Mercaptoacylamino derivatives of heterocyclic carboxylic acids
JPS604815B2 (ja)	1985-02-06	プロリン誘導体
JPS6121226B2 (fr)	1986-05-26
HU180529B (en)	1983-03-28	Process for producing cysteinyl-l-proline
CA1146940A (fr)	1983-05-24	Derives d'acides thiazolidinecarboxyliques et acides apparentes
US4154937A (en)	1979-05-15	Hydroxycarbamoylalkylacylpipecolic acid compounds
US4296033A (en)	1981-10-20	4-Azido-1-mercaptoacyl proline
CS199693B2 (cs)	1980-07-31	Způsob výroby derivátů thiazolidin-, thiazana morfolinkarboxylových kyselin
IE60995B1 (en)	1994-09-07	Process for the synthesis of alpha N alkylated amino acids and esters thereof. Application to the synthesis of carboxyalkyl dipeptides.
US4282235A (en)	1981-08-04	Derivatives of thiazolidinecarboxylic acids and related acids
EP0053017B1 (fr)	1985-02-20	Dérivés amidiques
US4198509A (en)	1980-04-15	Mercaptoacylpiperazine carboxylic acid compounds
US4988701A (en)	1991-01-29	Cyclic amino-thioacetal amides, a process for the preparation thereof and pharmaceutical compositions
CA1102812A (fr)	1981-06-09	Traduction non-disponible
US4237134A (en)	1980-12-02	Derivatives of thiazolidinecarboxylic acids and related acids
US4307110A (en)	1981-12-22	Mercaptoacyl derivatives of 3-substituted proline derivatives
US4308388A (en)	1981-12-29	4-Azido-1-mercaptoacyl pipecolic acid
GB2090591A (en)	1982-07-14	Amide derivatives
KR810000464B1 (ko)	1981-05-09	신규 치환칼복실산 유도체의 제조방법
KR800000920B1 (ko)	1980-09-12	아미노산의 치환된 아실 유도체의 제조방법