CH673279A5 - - Google Patents

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Info

Publication number: CH673279A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; salt; solution; theory
Prior art date: 1986-06-27

Application number

CH2372/87A

Other languages

German (de)

English (en)

Inventor

Janos Dr Fischer

Tamas Dr Fodor

Laszlo Dr Dobay

Bela Dr Stefko

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.)

1986-06-27

Filing date

1987-06-24

Publication date

1990-02-28

1987-06-24 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1990-02-28 Publication of CH673279A5 publication Critical patent/CH673279A5/de

Links

RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 13
-1 isothiuronium compound Chemical class 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
150000003839 salts Chemical class 0.000 description 25
239000000243 solution Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 17
150000001875 compounds Chemical class 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 11
229960000830 captopril Drugs 0.000 description 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012433 hydrogen halide Substances 0.000 description 6
229910000039 hydrogen halide Inorganic materials 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000000010 aprotic solvent Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
238000002955 isolation Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
229930182821 L-proline Natural products 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
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 description 2
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
ZFAIWAPKPKJWEP-YFKPBYRVSA-N (2s)-1-(2-sulfanylacetyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)CS ZFAIWAPKPKJWEP-YFKPBYRVSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
BUPXDXGYFXDDAA-UHFFFAOYSA-N 3-bromo-2-methylpropanoic acid Chemical compound BrCC(C)C(O)=O BUPXDXGYFXDDAA-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 1
NEDMOHHWRPHBAL-MERQFXBCSA-N benzyl (2s)-pyrrolidin-1-ium-2-carboxylate;chloride Chemical compound Cl.O=C([C@H]1NCCC1)OCC1=CC=CC=C1 NEDMOHHWRPHBAL-MERQFXBCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
231100000315 carcinogenic Toxicity 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012495 reaction gas Substances 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000725 suspension Substances 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
125000003396 thiol group Chemical group [H]S* 0.000 description 1
LVLIZZNOOLCRKZ-UHFFFAOYSA-N thiourea;hydrate Chemical compound O.NC(N)=S LVLIZZNOOLCRKZ-UHFFFAOYSA-N 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

CH2372/87A 1986-06-27 1987-06-24 CH673279A5 (it)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU862689A HU196959B (en)	1986-06-27	1986-06-27	Process for producing merkapto-acyl-proline derivatives

Publications (1)

Publication Number	Publication Date
CH673279A5 true CH673279A5 (it)	1990-02-28

Family

ID=10960651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH2372/87A CH673279A5 (it)	1986-06-27	1987-06-24

Country Status (21)

Country	Link
JP (1)	JPS6327475A (it)
KR (1)	KR900007217B1 (it)
CN (1)	CN87104388A (it)
AR (1)	AR243159A1 (it)
AT (2)	AT395012B (it)
CH (1)	CH673279A5 (it)
CS (1)	CS276394B6 (it)
DD (1)	DD263757A5 (it)
DE (1)	DE3721430A1 (it)
DK (1)	DK329787A (it)
ES (1)	ES2004451A6 (it)
FI (1)	FI87770C (it)
GR (1)	GR871012B (it)
HU (1)	HU196959B (it)
IT (1)	IT1206792B (it)
NO (1)	NO168941C (it)
PL (1)	PL153449B1 (it)
PT (1)	PT85190B (it)
SE (1)	SE462751B (it)
SU (1)	SU1650007A3 (it)
YU (1)	YU46319B (it)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE421551B (sv) *	1980-03-26	1982-01-04	Sandvik Ab	Borrverktyg for rotations- och/eller slagborrning
HU208954B (en) *	1990-09-21	1994-02-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing 1-(3-mercapto-(2s)-methyl-1-oxo-propyl)-l-prolyn
JPS62125081A (ja) *	1985-11-21	1987-06-06	キングプリンテイング株式会社	捺染方法
ES2182116T3 (es) *	1996-09-26	2003-03-01	Meditor Pharmaceuticals Ltd	Composiciones farmaceuticas que comprenden derivados del s-alquilisotiouronio.
CN103086939A (zh) *	2011-10-28	2013-05-08	华中药业股份有限公司	1-(3-溴-2-d-甲基丙酰基)吡咯烷-2-羧酸的重结晶方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU509899B2 (en) *	1976-02-13	1980-05-29	E.R. Squibb & Sons, Inc.	Proline derivatives and related compounds
IL58849A (en) *	1978-12-11	1983-03-31	Merck & Co Inc	Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them
GB2065643B (en) *	1979-12-13	1983-08-24	Kanegafuchi Chemical Ind	Optically active n-mercaptoalkanoylamino acids
IE54551B1 (en) *	1982-01-22	1989-11-22	Ici Plc	Amide derivatives
KR860001391B1 (ko) *	1984-07-23	1986-09-22	보령제약 주식회사	피롤리딘 유도체의 제조방법

1986
- 1986-04-07 AT AT0091186A patent/AT395012B/de not_active IP Right Cessation
- 1986-06-27 HU HU862689A patent/HU196959B/hu unknown
1987
- 1987-06-24 CH CH2372/87A patent/CH673279A5/de not_active IP Right Cessation
- 1987-06-24 CN CN198787104388A patent/CN87104388A/zh active Pending
- 1987-06-24 YU YU118187A patent/YU46319B/sh unknown
- 1987-06-26 PL PL1987266478A patent/PL153449B1/pl unknown
- 1987-06-26 GR GR871012A patent/GR871012B/el unknown
- 1987-06-26 PT PT85190A patent/PT85190B/pt not_active IP Right Cessation
- 1987-06-26 JP JP62159491A patent/JPS6327475A/ja active Pending
- 1987-06-26 CS CS874794A patent/CS276394B6/cs unknown
- 1987-06-26 ES ES8702024A patent/ES2004451A6/es not_active Expired
- 1987-06-26 IT IT8721085A patent/IT1206792B/it active
- 1987-06-26 SU SU874202836A patent/SU1650007A3/ru active
- 1987-06-26 AT AT0162087A patent/AT387381B/de not_active IP Right Cessation
- 1987-06-26 SE SE8702654A patent/SE462751B/sv not_active IP Right Cessation
- 1987-06-26 DK DK329787A patent/DK329787A/da not_active Application Discontinuation
- 1987-06-26 DD DD87304203A patent/DD263757A5/de not_active IP Right Cessation
- 1987-06-26 KR KR1019870006546A patent/KR900007217B1/ko active Pre-grant Review Request
- 1987-06-26 NO NO872690A patent/NO168941C/no unknown
- 1987-06-26 AR AR87307987A patent/AR243159A1/es active
- 1987-06-26 FI FI872859A patent/FI87770C/fi not_active IP Right Cessation
- 1987-06-29 DE DE19873721430 patent/DE3721430A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
SE462751B (sv)	1990-08-27
ATA162087A (de)	1988-06-15
CS276394B6 (en)	1992-05-13
DE3721430A1 (de)	1988-01-28
FI872859A (fi)	1987-12-28
YU118187A (en)	1988-04-30
KR880000392A (ko)	1988-03-25
NO168941C (no)	1992-04-29
YU46319B (sh)	1993-05-28
FI87770B (fi)	1992-11-13
SE8702654L (sv)	1987-12-28
DD263757A5 (de)	1989-01-11
IT1206792B (it)	1989-05-03
AT395012B (de)	1992-08-25
ATA91186A (de)	1992-01-15
CS479487A3 (en)	1992-01-15
CN87104388A (zh)	1988-03-02
AT387381B (de)	1989-01-10
FI87770C (fi)	1993-02-25
PL153449B1 (en)	1991-04-30
NO168941B (no)	1992-01-13
IT8721085A0 (it)	1987-06-26
AR243159A1 (es)	1993-07-30
PT85190B (pt)	1990-03-30
NO872690D0 (no)	1987-06-26
FI872859A0 (fi)	1987-06-26
ES2004451A6 (es)	1989-01-01
GR871012B (en)	1987-11-02
HU196959B (en)	1989-02-28
DK329787A (da)	1987-12-28
NO872690L (no)	1987-12-28
JPS6327475A (ja)	1988-02-05
PL266478A1 (en)	1988-06-09
DK329787D0 (da)	1987-06-26
KR900007217B1 (ko)	1990-10-05
SE8702654D0 (sv)	1987-06-26
SU1650007A3 (ru)	1991-05-15
HUT44490A (en)	1988-03-28
PT85190A (en)	1987-07-01

Publication	Publication Date	Title
DD155898A5 (de)	1982-07-14	Verfahren zur herstellung von 1-[3-mercapto-(2s)-methyl-propionyl]-pyrrolidin-(2s)-carbonsaeure
DE2820375C2 (it)	1991-01-17
CH597199A5 (en)	1978-03-31	3-Phenyl pyridaz-6-ones prodn.
CH673279A5 (it)	1990-02-28
EP0370391A2 (de)	1990-05-30	Verfahren zur Herstellung von 4,5-Dichlor-6-ethylpyrimidin
EP0150034A2 (de)	1985-07-31	2-Aminothiophenderivate
CH636332A5 (en)	1983-05-31	Process for preparing monoalkylated dihydroxybenzenes
DE2167320C2 (de)	1984-07-05	Verfahren zur Herstellung von 2-Mercapto-1,3,4-thiadiazolen
EP0134934B1 (de)	1987-03-04	2-Ketosulfonamide und Verfahren zu deren Herstellung
EP0057889A1 (de)	1982-08-18	Verfahren zur Herstellung von 1-Alkyl-2-chlor-5-nitro-4-benzol-sulfonsäuren
SU415869A3 (it)	1974-02-15
DE2856404A1 (de)	1980-07-17	1,2,3-thiadiazol-5-yl-thioglycolsaeure, deren derivate sowie verfahren zu deren herstellung
AT397086B (de)	1994-01-25	Verfahren zur herstellung von neuen 2-(2-aminothiazol-4-4yl)-2-(syn)-alkoxyimino- acetamiden
AT331804B (de)	1976-08-25	Verfahren zur herstellung von neuen 6-aza-3h-1,4-benzodiazepinen, deren optischen isomeren und deren salzen
AT263023B (de)	1968-07-10	Verfahren zur Herstellung von neuen Phenothiazinderivaten und ihren Salzen
AT336572B (de)	1977-05-10	Verfahren zur herstellung von neuen alkylsulfonylaminoglycinen sowie deren salzen
AT246117B (de)	1966-04-12	Verfahren zur Herstellung von 6,8-Dithiooctansäureamiden
EP0418662A1 (de)	1991-03-27	Verfahren zur Herstellung von 2-Alkylamino-4-aminobenzolsulfonsäuren
AT315195B (de)	1974-05-10	Verfahren zur Herstellung von neuen Thiocarbaminsäureestern und deren Alkali-, Erdalkali- oder Ammoniumsalzen
AT274802B (de)	1969-10-10	Verfahren zur Herstellung von Indolderivaten
CH667655A5 (de)	1988-10-31	Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen.
CH634046A5 (en)	1983-01-14	Process for preparing phenylalkylsulphones
CH415630A (de)	1966-06-30	Verfahren zur Herstellung von Picolinsäurederivaten
DE3914650A1 (de)	1990-11-08	Neue phenylendiamine sowie ein verfahren zur herstellung von phenylendiaminen
DE1210893B (de)	1966-02-17	Verfahren zur Herstellung von 6, 8-Dithiooctansaeureamiden

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