DD155898A5 - Verfahren zur herstellung von 1-[3-mercapto-(2s)-methyl-propionyl]-pyrrolidin-(2s)-carbonsaeure - Google Patents

Verfahren zur herstellung von 1-[3-mercapto-(2s)-methyl-propionyl]-pyrrolidin-(2s)-carbonsaeure Download PDF

Info

Publication number: DD155898A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; propionyl; proline; acid; carboxylic acid
Prior art date: 1979-12-29

Application number

DD80226586A

Other languages

German (de)

English (en)

Inventor

Janos Fischer

Laszlo Rozsa

Anna Bakonyi

Gabor Fazekas

Pal Vago

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1979-12-29

Filing date

1980-12-23

Publication date

1982-07-14

1980-12-23 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1982-07-14 Publication of DD155898A5 publication Critical patent/DD155898A5/de

Links

239000002253 acid Substances 0.000 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title 1
229910052799 carbon Inorganic materials 0.000 title 1
229960002429 proline Drugs 0.000 claims abstract description 28
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims abstract description 24
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 24
229930182821 L-proline Natural products 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 18
238000005917 acylation reaction Methods 0.000 claims abstract description 9
230000010933 acylation Effects 0.000 claims abstract description 8
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
239000007795 chemical reaction product Substances 0.000 claims abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
-1 alkali metal thiosulfate Chemical class 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
239000003513 alkali Substances 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
USAIOOFEIMNEDN-UHFFFAOYSA-L disodium;carbonotrithioate Chemical compound [Na+].[Na+].[S-]C([S-])=S USAIOOFEIMNEDN-UHFFFAOYSA-L 0.000 claims description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 2
235000019345 sodium thiosulphate Nutrition 0.000 claims description 2
238000002360 preparation method Methods 0.000 abstract description 7
125000001475 halogen functional group Chemical group 0.000 abstract description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
229910052794 bromium Inorganic materials 0.000 abstract 1
239000012467 final product Substances 0.000 abstract 1
230000001172 regenerating effect Effects 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
239000000243 solution Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
125000003396 thiol group Chemical group [H]S* 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000012736 aqueous medium Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
VFVHNRJEYQGRGE-UHFFFAOYSA-N 3-acetylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)C(C)CSC(C)=O VFVHNRJEYQGRGE-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
238000007792 addition Methods 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 2
JXGVXCZADZNAMJ-NSHDSACASA-N (2s)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-NSHDSACASA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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 1
MHRDCHHESNJQIS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropanoic acid Chemical compound SCC(C)C(O)=O MHRDCHHESNJQIS-UHFFFAOYSA-N 0.000 description 1
ZVDKTPOXSAEUQU-UHFFFAOYSA-N 3-bromo-2-methylpropanoyl chloride Chemical compound BrCC(C)C(Cl)=O ZVDKTPOXSAEUQU-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 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
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
XJJBXZIKXFOMLP-ZETCQYMHSA-N tert-butyl (2s)-pyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)[C@@H]1CCCN1 XJJBXZIKXFOMLP-ZETCQYMHSA-N 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
- C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms

Landscapes

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

DD80226586A 1979-12-29 1980-12-23 Verfahren zur herstellung von 1-[3-mercapto-(2s)-methyl-propionyl]-pyrrolidin-(2s)-carbonsaeure DD155898A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU79EE2720A HU184082B (en)	1979-12-29	1979-12-29	Process for preparing 1-3-/3mercapto-/2s/-methyl-propinyl/-pyrrolidine-/2s/-carboxylic acid

Publications (1)

Publication Number	Publication Date
DD155898A5 true DD155898A5 (de)	1982-07-14

Family

ID=10995884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80226586A DD155898A5 (de)	1979-12-29	1980-12-23	Verfahren zur herstellung von 1-[3-mercapto-(2s)-methyl-propionyl]-pyrrolidin-(2s)-carbonsaeure

Country Status (21)

Country	Link
US (1)	US4332725A (cs)
JP (1)	JPS6058230B2 (cs)
AT (1)	AT375340B (cs)
CA (1)	CA1137499A (cs)
CH (1)	CH646423A5 (cs)
CS (1)	CS219935B2 (cs)
DD (1)	DD155898A5 (cs)
DE (1)	DE3049273C2 (cs)
DK (1)	DK157009C (cs)
ES (1)	ES497458A0 (cs)
FI (1)	FI67693C (cs)
GB (1)	GB2066252B (cs)
GR (1)	GR72303B (cs)
HU (1)	HU184082B (cs)
NL (1)	NL186960C (cs)
NO (1)	NO154307C (cs)
PL (1)	PL130249B1 (cs)
PT (1)	PT72222B (cs)
SE (1)	SE440350B (cs)
SU (1)	SU1139374A3 (cs)
YU (1)	YU43485B (cs)

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Publication number	Priority date	Publication date	Assignee	Title
US4385062A (en) *	1980-01-09	1983-05-24	Gruppo Lepetit S.P.A.	1-[(-2-Mercaptocycloalkyl)carbonyl]-L-proline derivatives, the process for their manufacture, the intermediates for their synthesis and their use as anti-hypertensive agents
IE50839B1 (en) *	1980-02-26	1986-07-23	Wyeth John & Brother Ltd	Novel processes for preparing proline derivatives and analogous compounds
HU208954B (en) *	1990-09-21	1994-02-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing 1-(3-mercapto-(2s)-methyl-1-oxo-propyl)-l-prolyn
DE3124091C2 (de) *	1981-06-19	1983-06-01	Degussa Ag, 6000 Frankfurt	N-(3-Cyanopropanoyl)-aminocarbonsäureester und deren Verwendung
JPS58124764A (ja) *	1982-01-20	1983-07-25	Kanegafuchi Chem Ind Co Ltd	光学活性チオ−ル化合物の製造法
KR860001391B1 (ko) *	1984-07-23	1986-09-22	보령제약 주식회사	피롤리딘 유도체의 제조방법
KR870001570B1 (ko) *	1984-12-19	1987-09-04	보령제약 주식회사	피롤리딘 유도체의 제조방법
KR870001569B1 (ko) *	1985-02-11	1987-09-04	보령제약 주식회사	피롤리딘 유도체의 제조방법
HU196368B (en) *	1986-07-04	1988-11-28	Egyt Gyogyszervegyeszeti Gyar	Process for production of 1-/3-brom-/25/-methil-prophionil/-pirrolidin-/25/-carbonic acid
JPH026833A (ja) *	1988-06-24	1990-01-11	Nippon Alum Mfg Co Ltd	粉粒体混合装置
IL91581A (en) *	1988-09-13	1993-07-08	Sepracor Inc	Methods for preparing optically active captopril and its analogues
US5166361A (en) *	1988-09-13	1992-11-24	Sepracor, Inc.	Methods for preparing captopril and its analogues
US5026873A (en) *	1989-11-06	1991-06-25	E. R. Squibb & Sons, Inc.	Process for direct isolation of captopril
KR940005014B1 (ko) *	1991-11-07	1994-06-09	보령제약 주식회사	피롤리딘카르복실산 유도체의 제조방법
HUT64965A (en) *	1992-03-13	1994-03-28	Egyt Gyogyszervegyeszeti Gyar	Process for the production of 2-imino-selenazolydes and medical preparations containing them
CN102452970A (zh) *	2010-10-16	2012-05-16	华中药业股份有限公司	D-3-溴-2-甲基丙酰-l-脯氨酸的制备方法
CN103086940B (zh) *	2011-10-28	2014-07-09	华中药业股份有限公司	一种1-(3-巯基-2-d-甲基丙酰基)-l-脯氨酸的合成方法

Family Cites Families (7)

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Publication number	Priority date	Publication date	Assignee	Title
US4105776A (en) *	1976-06-21	1978-08-08	E. R. Squibb & Sons, Inc.	Proline derivatives and related compounds
US4241076A (en) *	1978-02-21	1980-12-23	E. R. Squibb & Sons, Inc.	Halogenated substituted mercaptoacylamino acids
CA1132985A (en) *	1978-12-22	1982-10-05	John Krapcho	Ketal and thioketal derivatives of mercaptoacyl prolines
US4181663A (en) *	1979-01-29	1980-01-01	E. R. Squibb & Sons, Inc.	Selenium containing derivatives of proline and pipecolic acid
US4297282A (en) *	1979-03-02	1981-10-27	Sumitomo Chemical Company, Limited	Resolution of mercaptopropionic acids
US4288368A (en) *	1979-07-30	1981-09-08	E. R. Squibb & Sons, Inc.	Dithioacylproline derivatives
US4284561A (en) *	1979-12-03	1981-08-18	E. R. Squibb & Sons, Inc.	Hydroxamic acid derivatives of mercaptoacyl amino acids

1979
- 1979-12-29 HU HU79EE2720A patent/HU184082B/hu unknown
1980
- 1980-11-28 AT AT0582080A patent/AT375340B/de not_active IP Right Cessation
- 1980-12-03 CA CA000366072A patent/CA1137499A/en not_active Expired
- 1980-12-04 ES ES497458A patent/ES497458A0/es active Granted
- 1980-12-04 NL NLAANVRAGE8006613,A patent/NL186960C/xx not_active IP Right Cessation
- 1980-12-15 SU SU803228098A patent/SU1139374A3/ru active
- 1980-12-18 SE SE8008942A patent/SE440350B/sv not_active IP Right Cessation
- 1980-12-18 PT PT72222A patent/PT72222B/pt not_active IP Right Cessation
- 1980-12-18 CS CS809026A patent/CS219935B2/cs unknown
- 1980-12-22 US US06/218,814 patent/US4332725A/en not_active Expired - Lifetime
- 1980-12-23 DD DD80226586A patent/DD155898A5/de unknown
- 1980-12-23 PL PL1980228689A patent/PL130249B1/pl unknown
- 1980-12-23 FI FI804016A patent/FI67693C/fi not_active IP Right Cessation
- 1980-12-23 DK DK553680A patent/DK157009C/da not_active IP Right Cessation
- 1980-12-23 GR GR63748A patent/GR72303B/el unknown
- 1980-12-23 NO NO803939A patent/NO154307C/no unknown
- 1980-12-24 CH CH956480A patent/CH646423A5/de unknown
- 1980-12-24 YU YU3259/80A patent/YU43485B/xx unknown
- 1980-12-29 DE DE3049273A patent/DE3049273C2/de not_active Expired
- 1980-12-29 GB GB8041403A patent/GB2066252B/en not_active Expired
- 1980-12-29 JP JP55189498A patent/JPS6058230B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE3049273C2 (de)	1985-06-05
DK157009C (da)	1990-03-26
ES8200340A1 (es)	1981-11-16
DE3049273A1 (de)	1981-12-24
AT375340B (de)	1984-07-25
PL130249B1 (en)	1984-07-31
DK157009B (da)	1989-10-30
NL8006613A (nl)	1981-08-03
FI67693B (fi)	1985-01-31
GB2066252B (en)	1983-11-23
PT72222A (en)	1981-01-01
SE8008942L (sv)	1981-06-30
NO154307B (no)	1986-05-20
SU1139374A3 (ru)	1985-02-07
NO154307C (no)	1986-08-27
NL186960C (nl)	1991-04-16
FI67693C (fi)	1986-06-10
SE440350B (sv)	1985-07-29
JPS56100760A (en)	1981-08-12
PL228689A1 (cs)	1981-08-07
NL186960B (nl)	1990-11-16
FI804016L (fi)	1981-06-24
US4332725A (en)	1982-06-01
ATA582080A (de)	1983-12-15
GR72303B (cs)	1983-10-18
CA1137499A (en)	1982-12-14
GB2066252A (en)	1981-07-08
YU325980A (en)	1983-01-21
JPS6058230B2 (ja)	1985-12-19
PT72222B (en)	1981-11-02
YU43485B (en)	1989-08-31
CS219935B2 (en)	1983-03-25
ES497458A0 (es)	1981-11-16
CH646423A5 (de)	1984-11-30
NO803939L (no)	1981-06-30
HU184082B (en)	1984-06-28
DK553680A (da)	1981-06-30

Publication	Publication Date	Title
DD129442B3 (de)	1990-01-10	Verfahren zur herstellung von captopril und vertraeglichen salzen
US4154935A (en)	1979-05-15	Halogen substituted mercaptoacylamino acids
CH646423A5 (de)	1984-11-30	Verfahren zur herstellung von 1-(3-mercapto-(2s)-methyl-propionyl)-pyrrolidin-(2s)-carbonsaeure.
DD283998A5 (de)	1990-10-31	Verfahren zur herstellung von prolinderivaten und verwandten verbindungen
DD141670A5 (de)	1980-05-14	Verfahren zur herstellung von aminosaeurederivaten
DD251750A5 (de)	1987-11-25	Verfahren zur herstellung von 1,2-dithiolan-3-pentansaeure (thioctsaeure)
DE3046271C2 (cs)	1988-07-28
DE3132332C2 (cs)	1989-12-14
DE3003145A1 (de)	1980-08-07	Mercaptoacylpyrrolidin- und mercaptoacylpiperidinphophonsaeurederivate
DE3721430A1 (de)	1988-01-28	Verfahren zur herstellung von 1-(3'-(mercapto)-(2's)-(methyl)-propionyl)-pyrrolidin-(2s)-carbonsaeure oder ihren salzen
DD142876A5 (de)	1980-07-16	Verfahren zur herstellung von pyrrolidincarboxaldehyd-und piperidincarboxaldehyd-derivaten
DE2642608C2 (de)	1987-03-19	Verfahren zur Herstellung eines 4-Hydroxymethyl-2-pyrrolidinons
DE3538747C2 (cs)	1988-08-18
DE2065698A1 (de)	1974-12-12	Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon
CH628634A5 (de)	1982-03-15	Verfahren zur herstellung von 2,2'-bis(3,4-epoxy-5-oxotetrahydropyran)aether und produkt.
DE3526023C2 (cs)	1988-10-20
DE3310174C2 (de)	1997-02-06	Verfahren zur Herstellung von Hydroxyäthyltetrazolthiol
AT358178B (de)	1980-08-25	Verfahren zur herstellung von neuen keteniminen
EP0046138B1 (de)	1985-12-04	Verfahren zur Herstellung von 3-(N-Arylamino)-tetrahydrothiophen-2-on-derivaten
US5371238A (en)	1994-12-06	Process for producing azacycloalkane derivatives
AT274802B (de)	1969-10-10	Verfahren zur Herstellung von Indolderivaten
AT246117B (de)	1966-04-12	Verfahren zur Herstellung von 6,8-Dithiooctansäureamiden
AT379152B (de)	1985-11-25	Verfahren zur herstellung von 3-(n-aryl-nacylamino)-gamma- butyrothiolactonen
AT283348B (de)	1970-08-10	Verfahren zur Herstellung von Indolderivaten und ihren neuen Salzen
DE1470197C (de)	1973-05-03	alpha.alpha Diphenyl alpha eckige Klammer auf 1 methylpyrrohdyl (3) eckige Klammer zu N,N dimethylace tamid und seine pharmakologisch ge eigneten Saureanlagerungssalze sowie Verfahren zur Herstellung dieser Ver bindungen