SU955857A3 - Способ получени меркаптоациламинокислот или их солей - Google Patents
Способ получени меркаптоациламинокислот или их солей Download PDFInfo
- Publication number
- SU955857A3 SU955857A3 SU782632596A SU2632596A SU955857A3 SU 955857 A3 SU955857 A3 SU 955857A3 SU 782632596 A SU782632596 A SU 782632596A SU 2632596 A SU2632596 A SU 2632596A SU 955857 A3 SU955857 A3 SU 955857A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- salts
- alkyl
- producing
- hydrogen
- acids
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- 239000002253 acid Substances 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 title claims description 6
- 150000007513 acids Chemical class 0.000 title claims description 5
- 150000001413 amino acids Chemical class 0.000 claims abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Chemical group CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Chemical group CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- -1 thio acid chloride Chemical compound 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 abstract 3
- 241000124008 Mammalia Species 0.000 abstract 2
- 230000001631 hypertensive effect Effects 0.000 abstract 2
- 239000005541 ACE inhibitor Substances 0.000 abstract 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 abstract 1
- 102000015427 Angiotensins Human genes 0.000 abstract 1
- 108010064733 Angiotensins Proteins 0.000 abstract 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 abstract 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 2
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ МЕРКАПТОАЦИЛАМИНОКИСЛОТ Изобретение относитс к способу получени новых производных меркаптоациламинокислот форму.пы | Вг Ri Е jd О-$-dHz-dH-И (-кн--с н-|й , где Ryj - водород, С.|-C-j-алкил, замещенный фенилом, оксифенилом, индолом или гуанидином, RX - водород или С -С -алкил; R, -С2.-алкил, или их солей CllИзвестные соединени обладают свойствами снижать или ослабл ть повышенное давление, св занное с применением противогипертонических лекарственных препаратов, в частности, антиотензнна. Способ получени соединений фО1 «улы (I) основан на известной реакции .взаимодействи хлорангидридов кислот с соответствующими кислотами в среде инертного органического растворител . в широком температурном интервале ведени процесса (от пониженных температур Jao превышающих ) . . Цель изобретени - расширение ас сортимента средств, воздействующих на живой организм.
ИЛИ ИХ СОЛЕЙ Поставленна цель достигаетс способом получени меркаптоациламинокислот общей формулы (t), заключающимс в том, что хлорид тиокислоты формулы . Б 3 dH-dOOH где RJI % имеют указанные значени, подвергают взаимодействию с аминокисl лотой форму.пы H N-CH-COOH, где R имеет указанные значени , процесс ведут в водном растворе карбоната натри с последукадим выделением целевого . продукта в свободном эиде или в виде соли. П р и м е р i. (3-ацетилтио-2-метилпропаноил )-L-аргинин. L-арЕИНИн (2,61 г) раствор ют в смеси карбоната натри (3,2 г) и воды (30 мл) и раствор охлаждают в лед ной бане. Добавл ют 3-ацетилтио-2-метилпропаноилхлорид (2,7 г), и реакционную смесь перемешивают при комнатной температуре в течение 1,5 ч. Добавл ют 50 мл ионообменной СМО.ПЫ (AG 50W) и суспензию загружают в колонку с этой же смолой (ВО мл).
Claims (1)
- Формула изобретенияСпособ получения меркаптоациламинокислот общей формулы 1 .· »1 tHi-tiH-CO-NR-dH-COOH6де - водород; С4-С j-алкил, замеенный фенилом, оксифенилом, индолом или гуанидином; R1. - водород или С4-Сг-алкил, R5-C4-С^-алкил, или их солей, заключающийся в теми, что хлорид тиокислоты формулы .ж э <*о- $ -· Си -еоон it . ’ где 8¾имеют указанные значения, подвергают взаимодействию с аминокислотой формулы где 84 имеет указанные значения, и процесс ведут в водном растворе карбоната натрия с последующим выделением целевого продукта в свободном виде или в виде соли.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/684,606 US4053651A (en) | 1976-05-10 | 1976-05-10 | Compounds and method for alleviating angiotensin related hypertension |
Publications (1)
Publication Number | Publication Date |
---|---|
SU955857A3 true SU955857A3 (ru) | 1982-08-30 |
Family
ID=24748765
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU772478851A SU818479A3 (ru) | 1976-05-10 | 1977-05-10 | Способ получени меркаптоацилами-НОКиСлОТ |
SU782632596A SU955857A3 (ru) | 1976-05-10 | 1978-07-05 | Способ получени меркаптоациламинокислот или их солей |
SU782632600A SU697049A3 (ru) | 1976-05-10 | 1978-07-05 | Способ получени меркаптоациламинокислот или их солей |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU772478851A SU818479A3 (ru) | 1976-05-10 | 1977-05-10 | Способ получени меркаптоацилами-НОКиСлОТ |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU782632600A SU697049A3 (ru) | 1976-05-10 | 1978-07-05 | Способ получени меркаптоациламинокислот или их солей |
Country Status (21)
Country | Link |
---|---|
US (2) | US4053651A (ru) |
JP (1) | JPS52136117A (ru) |
AU (1) | AU513622B2 (ru) |
BE (1) | BE854458A (ru) |
CA (1) | CA1119177A (ru) |
CH (2) | CH620202A5 (ru) |
CS (1) | CS204001B2 (ru) |
DD (1) | DD130477A5 (ru) |
DE (1) | DE2717548A1 (ru) |
DK (1) | DK203177A (ru) |
FR (2) | FR2372624A1 (ru) |
GB (1) | GB1577415A (ru) |
HU (1) | HU177750B (ru) |
IE (1) | IE44821B1 (ru) |
NL (1) | NL7704712A (ru) |
NO (1) | NO771623L (ru) |
PL (2) | PL107991B1 (ru) |
SE (1) | SE7705382L (ru) |
SU (3) | SU818479A3 (ru) |
YU (1) | YU116877A (ru) |
ZA (1) | ZA772256B (ru) |
Families Citing this family (113)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS535112A (en) * | 1976-03-08 | 1978-01-18 | Santen Pharmaceutical Co Ltd | New cysteine derivatives |
US4140786A (en) * | 1976-05-10 | 1979-02-20 | E. R. Squibb & Sons, Inc. | Method for alleviating angiotensin related hypertension |
US4339600A (en) * | 1976-05-10 | 1982-07-13 | E. R. Squibb & Sons, Inc. | Compounds for alleviating angiotensin related hypertension |
US4091024A (en) * | 1976-12-03 | 1978-05-23 | E. R. Squibb & Sons, Inc. | Pyrrolidine and piperidine-2-carboxylic acid derivatives |
US4175199A (en) * | 1976-12-03 | 1979-11-20 | E. R. Squibb & Sons, Inc. | Substituted acyl derivatives of amino acids |
US4176235A (en) * | 1976-12-03 | 1979-11-27 | E. R. Squibb & Sons, Inc. | Substituted acyl derivatives of amino acids |
US4178291A (en) * | 1976-12-03 | 1979-12-11 | E. R. Squibb & Sons, Inc. | Substituted acyl derivatives of amino acids |
US4116962A (en) * | 1976-12-03 | 1978-09-26 | E. R. Squibb & Sons, Inc. | Pyrrolidine and piperidine-2-carboxylic acid derivatives |
US4206121A (en) * | 1976-12-03 | 1980-06-03 | E. R. Squibb & Sons, Inc. | Substituted acyl derivatives of amino acids |
US4113715A (en) * | 1977-01-17 | 1978-09-12 | E. R. Squibb & Sons, Inc. | Amino acid derivatives |
US4611002A (en) * | 1977-07-14 | 1986-09-09 | E. R. Squibb And Sons, Inc. | Carboxymethyl esters of mercaptopropanoic acids as enkephalinase inhibitors |
US4206137A (en) * | 1978-03-27 | 1980-06-03 | E. R. Squibb & Sons, Inc. | Thioalkanoylalkanoic acid compounds |
US4927853A (en) * | 1978-04-24 | 1990-05-22 | Massachusetts Institute Of Technology | Composition for increasing blood pressure |
US4698355A (en) * | 1979-08-14 | 1987-10-06 | University Of Miami | Anti-hypertensive agents |
US4690940A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
US4698356A (en) * | 1979-08-14 | 1987-10-06 | University Of Miami | Anti-hypertensive agents |
US4695577A (en) * | 1979-08-14 | 1987-09-22 | University Of Miami | Anti-hypertensive agents |
US4690937A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
US4690939A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
GR73585B (ru) * | 1978-09-11 | 1984-03-26 | Univ Miami | |
ZA794723B (en) * | 1978-09-11 | 1980-08-27 | Univ Miami | Anti-hypertensive agents |
US4690938A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
JPS6058908B2 (ja) * | 1978-10-11 | 1985-12-23 | 参天製薬株式会社 | システイン誘導体 |
JPS6011888B2 (ja) * | 1978-10-11 | 1985-03-28 | 参天製薬株式会社 | リウマチ疾患治療薬 |
US4211786A (en) * | 1979-03-08 | 1980-07-08 | E. R. Squibb & Sons, Inc. | Mercaptoacyldihydropyrazole carboxylic acid derivatives |
US4235885A (en) * | 1979-06-25 | 1980-11-25 | E. R. Squibb & Sons, Inc. | Inhibitors of mammalian collagenase |
US4256761A (en) * | 1979-07-13 | 1981-03-17 | Usv Pharmaceutical Corporation | Antihypertensive amides |
US4549992A (en) * | 1979-07-13 | 1985-10-29 | Usv Pharmaceutical Corp. | Antihypertensive amides |
US4565825A (en) * | 1979-07-13 | 1986-01-21 | Usv Pharmaceutical Corp. | Antihypertensive N-benzimidazolyl- and N-imidazolyl-amino acid derivatives |
DE2951353A1 (de) * | 1979-12-20 | 1981-07-02 | Basf Ag, 6700 Ludwigshafen | Kationische farbstoffe |
PT70158A1 (en) * | 1980-03-03 | 1982-03-01 | Univ Miami | Process for preparing anti-hypertensive agents |
US4690936A (en) * | 1980-03-05 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
US4692458A (en) * | 1980-03-05 | 1987-09-08 | University Of Miami | Anti-hypertensive agents |
US4734420A (en) * | 1980-03-05 | 1988-03-29 | University Of Miami | Anti-hypertensive agents |
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 |
FR2480747A1 (fr) * | 1980-04-17 | 1981-10-23 | Roques Bernard | Derives d'acides amines et leur application therapeutique |
ZA811340B (en) * | 1980-06-09 | 1982-03-31 | Morton Norwich Products Inc | N-(cycloalkyl)amino acid compounds |
AU543804B2 (en) * | 1980-10-31 | 1985-05-02 | Takeda Chemical Industries Ltd. | Amides having bicyclic substituents on nitrogen |
US4521607A (en) * | 1981-02-27 | 1985-06-04 | Takeda Chemical Industries, Ltd. | Chromanyl glycines |
JPS57142962A (en) * | 1981-02-28 | 1982-09-03 | Santen Pharmaceut Co Ltd | Cyclodextrin clathrate compound of sulfur-containing compound |
US4329495A (en) * | 1981-05-18 | 1982-05-11 | Pfizer Inc. | Enkephalinase enzyme inhibiting compounds |
US4432971A (en) * | 1981-08-03 | 1984-02-21 | E. R. Squibb & Sons, Inc. | Phosphonamidate compounds |
US4432972A (en) * | 1981-08-03 | 1984-02-21 | E. R. Squibb & Sons, Inc. | Phosphonamidate compounds |
US4401677A (en) * | 1981-10-09 | 1983-08-30 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
US4474795A (en) * | 1981-10-09 | 1984-10-02 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
US4474799A (en) * | 1981-10-09 | 1984-10-02 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
US4396772A (en) * | 1981-11-23 | 1983-08-02 | F. R. Squibb & Sons, Inc. | Phosphinylalkanoyl amino acids |
IT1140394B (it) * | 1981-12-23 | 1986-09-24 | Maggioni Farma | Dipeptidi contenenti un residuo di metionina ad attivita' epatoprotettrice |
US4555506A (en) * | 1981-12-24 | 1985-11-26 | E. R. Squibb & Sons, Inc. | Phosphorus containing compounds and use as hypotensives |
JPS58140065A (ja) * | 1982-02-10 | 1983-08-19 | Meito Sangyo Kk | メルカプトベンジル脂肪酸誘導体類及びその製法 |
US4560680A (en) * | 1982-03-15 | 1985-12-24 | E. R. Squibb & Sons, Inc. | Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors |
US4452791A (en) * | 1982-03-15 | 1984-06-05 | E. R. Squibb & Sons, Inc. | Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors |
US4452790A (en) * | 1982-06-23 | 1984-06-05 | E. R. Squibb & Sons, Inc. | Phosphonyl hydroxyacyl amino acid derivatives as antihypertensives |
US4703043A (en) * | 1982-06-23 | 1987-10-27 | E. R. Squibb & Sons, Inc. | Phosphonyl hydroxyacyl amino acid derivatives as antihypertensive |
US4616005A (en) * | 1982-06-23 | 1986-10-07 | E. R. Squibb & Sons, Inc. | Phosphonyl hydroxyacyl amino acid derivatives as antihypertensives |
US4470973A (en) * | 1982-07-19 | 1984-09-11 | E. R. Squibb & Sons, Inc. | Substituted peptide compounds |
US4736066A (en) * | 1982-07-19 | 1988-04-05 | E. R. Squibb & Sons, Inc. | Intermediate for substituted peptide compounds |
US4661515A (en) * | 1982-07-21 | 1987-04-28 | Usv Pharmaceutical Corporation | Compounds having angiotensin converting enzyme inhibitory activity and diuretic activity |
IL69228A0 (en) * | 1982-07-21 | 1983-11-30 | Usv Pharma Corp | Compounds having diuretic activity and angiotensin converting inhibitory activity,methods of the preparation thereof and pharmaceutical compositions containing the same |
US4623729A (en) | 1982-07-22 | 1986-11-18 | E. R. Squibb & Sons, Inc. | Acylalkylaminocarbonyl substituted amino and imino acid compounds |
US4742067A (en) * | 1982-07-22 | 1988-05-03 | E. R. Squibb & Sons, Inc. | Acylalkylaminocarbonyl substituted amino and imino acid compounds |
US4621092A (en) * | 1982-07-22 | 1986-11-04 | E. R. Squibb & Sons, Inc. | Substituted proline compounds, composition and method of use |
US4524212A (en) * | 1982-09-27 | 1985-06-18 | E. R. Squibb & Sons, Inc. | Acyloxyketone substituted imino and amino acids |
FR2540495B1 (fr) * | 1983-02-07 | 1986-02-14 | Roussel Uclaf | Nouveaux derives de o-mercaptopropanamide et de ses homologues, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
US4774256A (en) * | 1983-10-03 | 1988-09-27 | E. R. Squibb & Sons, Inc. | Use of enkephalinase inhibitors as analgesic agents |
US4798904A (en) * | 1983-10-03 | 1989-01-17 | E. R. Squibb & Sons, Inc. | Certain [(lower alkanoyl-thio)methyl-1-oxo-3-phenyl propyl amino]benzene lower alkanoic acid or ester derivatives which inhibit enkephalinase |
US4722810A (en) * | 1984-08-16 | 1988-02-02 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
US4595700A (en) * | 1984-12-21 | 1986-06-17 | G. D. Searle & Co. | Thiol based collagenase inhibitors |
US4801609B1 (en) * | 1987-03-27 | 1993-11-09 | Mercapto-acylamino acid antihypertensives | |
US4929641B1 (en) * | 1988-05-11 | 1994-08-30 | Schering Corp | Mercapto-acylamino acid antihypertensives |
EP0254032A3 (en) * | 1986-06-20 | 1990-09-05 | Schering Corporation | Neutral metalloendopeptidase inhibitors in the treatment of hypertension |
US5262436A (en) * | 1987-03-27 | 1993-11-16 | Schering Corporation | Acylamino acid antihypertensives in the treatment of congestive heart failure |
CA1337400C (en) * | 1987-06-08 | 1995-10-24 | Norma G. Delaney | Inhibitors of neutral endopeptidase |
EP0318859A3 (en) * | 1987-12-03 | 1990-08-16 | Dainippon Pharmaceutical Co., Ltd. | N-substituted mercaptopropanamide derivatives |
US5210266A (en) * | 1987-12-03 | 1993-05-11 | Dainippon Pharmaceutical Co., Ltd. | N-substituted mercaptopropanamide derivatives |
US5179125A (en) * | 1987-12-03 | 1993-01-12 | Dainippon Pharmaceutical Co., Ltd. | N-substituted mercaptopropanamide derivatives |
US5292926A (en) * | 1988-01-25 | 1994-03-08 | Santen Pharmaceutical Co., Ltd. | Cysteine derivatives |
US5356890A (en) * | 1988-06-15 | 1994-10-18 | Brigham And Women's Hospital | S-nitroso derivatives of ace inhibitors and the use thereof |
US5002964A (en) * | 1988-06-15 | 1991-03-26 | Brigham & Women's Hospital | S-nitrosocaptopril compounds and the use thereof |
US5187183A (en) * | 1988-06-15 | 1993-02-16 | Brigham & Women's Hospital | S-nitroso derivatives of ACE inhibitors and the use thereof |
US5025001A (en) * | 1988-06-15 | 1991-06-18 | Brigham And Women's Hospital | S-nitroso derivatives of ACE inhibitors and the use thereof |
US4879309A (en) * | 1988-09-27 | 1989-11-07 | Schering Corporation | Mercapto-acylamino acids as antihypertensives |
ZA902661B (en) * | 1989-04-10 | 1991-01-30 | Schering Corp | Mercapto-acyl amino acids |
AU632596B2 (en) * | 1989-08-21 | 1993-01-07 | E.R. Squibb & Sons, Inc. | Phosphonate substituted amino or imino acids useful as antihypertensives |
WO1991009840A1 (en) * | 1989-12-22 | 1991-07-11 | Schering Corporation | Mercaptocycloacyl aminoacid endopeptidase inhibitors |
WO1991017980A1 (en) * | 1990-05-17 | 1991-11-28 | Schering Corporation | Disulfide derivatives of mercaptoacylamino acids |
FR2679564A1 (fr) * | 1991-07-23 | 1993-01-29 | Inst Nat Sante Rech Med | Nouveaux acylmercaptoalcanoldipeptides, leur preparation et les compositions qui les contiennent. |
US5504080A (en) * | 1992-10-28 | 1996-04-02 | Bristol-Myers Squibb Co. | Benzo-fused lactams |
US5424447A (en) * | 1993-07-07 | 1995-06-13 | The Medical College Of Wisconsin Research Foundation, Inc. | Heme binding compounds and use thereof |
FR2712286B1 (fr) * | 1993-11-12 | 1995-12-22 | Oreal | Nouveaux N-mercaptoalkyl alcanediamines et leur utilisation. |
DE4430023A1 (de) * | 1994-08-24 | 1996-02-29 | Boehringer Mannheim Gmbh | Elektrochemischer Sensor |
IT1273455B (it) * | 1995-01-27 | 1997-07-08 | Zambon Spa | Derivati tiolici ad attivita' inibitrice delle metallopeptidasi |
US5670545A (en) * | 1996-02-09 | 1997-09-23 | Board Of Regents Of The University Of Colorado | Method for the treatment of ischemic disease and reperfusion injury and the prevention of the adverse effects of reactive oxygen species |
FR2745571B1 (fr) * | 1996-03-04 | 1998-06-19 | Inst Nat Sante Rech Med | Nouveaux derives soufres comportant une liaison amide, leur procede de preparation, leur application a titre de medicaments, et les compositions pharmaceutiques les renfermant |
GB0221169D0 (en) | 2002-09-12 | 2002-10-23 | Univ Bath | Crystal |
GB0600406D0 (en) | 2006-01-10 | 2006-02-15 | Univ Bath | Crystal |
US9259535B2 (en) | 2006-06-22 | 2016-02-16 | Excelsior Medical Corporation | Antiseptic cap equipped syringe |
US11229746B2 (en) | 2006-06-22 | 2022-01-25 | Excelsior Medical Corporation | Antiseptic cap |
US9078992B2 (en) | 2008-10-27 | 2015-07-14 | Pursuit Vascular, Inc. | Medical device for applying antimicrobial to proximal end of catheter |
RU2572830C2 (ru) * | 2010-03-17 | 2016-01-20 | Акцо Нобель Кемикалз Интернэшнл Б.В. | Способ деполимеризации полисульфидов и получения простых бисмеркаптодиэфиров |
CA2841832C (en) | 2011-07-12 | 2019-06-04 | Pursuit Vascular, Inc. | Device for delivery of antimicrobial agent into a trans-dermal catheter |
US10046156B2 (en) | 2014-05-02 | 2018-08-14 | Excelsior Medical Corporation | Strip package for antiseptic cap |
PL224139B1 (pl) | 2014-08-01 | 2016-11-30 | Ekobenz Spółka Z Ograniczoną Odpowiedzialnością | Mieszanka paliwowa szczególnie do silników z zapłonem iskrowym |
JP6822978B2 (ja) | 2015-05-08 | 2021-01-27 | アイシーユー・メディカル・インコーポレーテッド | 治療薬のエミッタを受け入れるように構成された医療用コネクタ |
PL3525865T3 (pl) | 2016-10-14 | 2023-02-06 | Icu Medical, Inc. | Nasadki dezynfekcyjne dla łączników medycznych |
WO2018204206A2 (en) | 2017-05-01 | 2018-11-08 | Icu Medical, Inc. | Medical fluid connectors and methods for providing additives in medical fluid lines |
US11400195B2 (en) | 2018-11-07 | 2022-08-02 | Icu Medical, Inc. | Peritoneal dialysis transfer set with antimicrobial properties |
US11541220B2 (en) | 2018-11-07 | 2023-01-03 | Icu Medical, Inc. | Needleless connector with antimicrobial properties |
US11541221B2 (en) | 2018-11-07 | 2023-01-03 | Icu Medical, Inc. | Tubing set with antimicrobial properties |
US11534595B2 (en) | 2018-11-07 | 2022-12-27 | Icu Medical, Inc. | Device for delivering an antimicrobial composition into an infusion device |
US11517732B2 (en) | 2018-11-07 | 2022-12-06 | Icu Medical, Inc. | Syringe with antimicrobial properties |
US11433215B2 (en) | 2018-11-21 | 2022-09-06 | Icu Medical, Inc. | Antimicrobial device comprising a cap with ring and insert |
EP4255552A1 (en) | 2020-12-07 | 2023-10-11 | ICU Medical, Inc. | Peritoneal dialysis caps, systems and methods |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH451186A (de) * | 1961-11-02 | 1968-05-15 | Santen Phamarceutical Co Ltd | Verfahren zur Herstellung von N-Mercaptopropionylglycin und dessen Derivaten |
CA1009252A (en) | 1972-10-03 | 1977-04-26 | Santen Pharmaceutical Co. | N-(mercaptoacyl) aminoacids |
US3857951A (en) * | 1973-09-14 | 1974-12-31 | Cassenne Lab Sa | Use of 2-mercaptopropionylglycine and its alkali metal salts in treating respiratory diseases |
AU509899B2 (en) | 1976-02-13 | 1980-05-29 | E.R. Squibb & Sons, Inc. | Proline derivatives and related compounds |
-
1976
- 1976-05-10 US US05/684,606 patent/US4053651A/en not_active Expired - Lifetime
-
1977
- 1977-03-03 US US05/773,865 patent/US4112119A/en not_active Expired - Lifetime
- 1977-04-07 AU AU24106/77A patent/AU513622B2/en not_active Expired
- 1977-04-13 ZA ZA00772256A patent/ZA772256B/xx unknown
- 1977-04-13 CA CA000276034A patent/CA1119177A/en not_active Expired
- 1977-04-14 GB GB15559/77A patent/GB1577415A/en not_active Expired
- 1977-04-14 IE IE783/77A patent/IE44821B1/en not_active IP Right Cessation
- 1977-04-20 DE DE19772717548 patent/DE2717548A1/de active Granted
- 1977-04-21 CS CS772657A patent/CS204001B2/cs unknown
- 1977-04-29 NL NL7704712A patent/NL7704712A/xx not_active Application Discontinuation
- 1977-05-03 DD DD7700198728A patent/DD130477A5/xx unknown
- 1977-05-04 FR FR7713595A patent/FR2372624A1/fr active Granted
- 1977-05-07 PL PL1977197963A patent/PL107991B1/pl unknown
- 1977-05-07 PL PL1977205447A patent/PL106032B1/pl unknown
- 1977-05-09 YU YU01168/77A patent/YU116877A/xx unknown
- 1977-05-09 CH CH576677A patent/CH620202A5/fr not_active IP Right Cessation
- 1977-05-09 DK DK203177A patent/DK203177A/da unknown
- 1977-05-09 SE SE7705382A patent/SE7705382L/xx not_active Application Discontinuation
- 1977-05-09 NO NO771623A patent/NO771623L/no unknown
- 1977-05-09 HU HU77SU947A patent/HU177750B/hu unknown
- 1977-05-10 SU SU772478851A patent/SU818479A3/ru active
- 1977-05-10 BE BE177439A patent/BE854458A/xx not_active IP Right Cessation
- 1977-05-10 JP JP5420177A patent/JPS52136117A/ja active Granted
-
1978
- 1978-01-18 FR FR7801417A patent/FR2367741A1/fr active Granted
- 1978-07-05 SU SU782632596A patent/SU955857A3/ru active
- 1978-07-05 SU SU782632600A patent/SU697049A3/ru active
-
1980
- 1980-05-22 CH CH402580A patent/CH621763A5/fr not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
FR2367741A1 (fr) | 1978-05-12 |
GB1577415A (en) | 1980-10-22 |
HU177750B (en) | 1981-12-28 |
BE854458A (fr) | 1977-11-10 |
JPS6120544B2 (ru) | 1986-05-22 |
FR2372624A1 (fr) | 1978-06-30 |
SE7705382L (sv) | 1977-11-11 |
DK203177A (da) | 1977-11-11 |
DD130477A5 (de) | 1978-04-05 |
US4053651A (en) | 1977-10-11 |
CS204001B2 (en) | 1981-03-31 |
JPS52136117A (en) | 1977-11-14 |
IE44821L (en) | 1977-11-10 |
SU818479A3 (ru) | 1981-03-30 |
IE44821B1 (en) | 1982-04-07 |
DE2717548A1 (de) | 1977-12-01 |
ZA772256B (en) | 1978-03-29 |
YU116877A (en) | 1982-08-31 |
CH621763A5 (ru) | 1981-02-27 |
PL106032B1 (pl) | 1979-11-30 |
NL7704712A (nl) | 1977-11-14 |
AU2410677A (en) | 1978-10-12 |
PL197963A1 (pl) | 1978-03-28 |
AU513622B2 (en) | 1980-12-11 |
CH620202A5 (ru) | 1980-11-14 |
DE2717548C2 (ru) | 1990-05-03 |
SU697049A3 (ru) | 1979-11-05 |
FR2372624B1 (ru) | 1980-05-09 |
CA1119177A (en) | 1982-03-02 |
US4112119A (en) | 1978-09-05 |
PL107991B1 (pl) | 1980-03-31 |
FR2367741B1 (ru) | 1982-10-29 |
NO771623L (no) | 1977-11-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SU955857A3 (ru) | Способ получени меркаптоациламинокислот или их солей | |
DE69309686T2 (de) | Hydroxamsaürederivate als mettalloproteinase-inhibitoren | |
CA1040206A (en) | Phenylsulphinyl-amidine derivatives | |
SU648103A3 (ru) | Способ получени тетразол - (1,5-а) хинолинов или их солей | |
CS241016B2 (en) | Method of new n-(2-(or)pyrrolidinylmethyl)-benzamides production substituted in positions 2,3,4,5,6 | |
AU632044B2 (en) | Process for preparing a substituted or an unsubstituted 4(5)-(omega-aminoalkyl)imidazole | |
CA1109077A (en) | 2-hydrazonopropionic acid derivatives and the preparation thereof | |
US20200377456A1 (en) | Process for the preparation of glycopyrrolate tosylate | |
US4259525A (en) | Methionine process | |
US2312878A (en) | Alkali metal salts of beta-sulphopropionitrile and method of preparation | |
US3121111A (en) | Novel 4-thiohydantoic acids | |
US3423424A (en) | 3-phenyl-4-dialkylaminoalkyl-pyrazol-5-ol compounds | |
SU701535A3 (ru) | Способ получени производных 1,2,4-триазола или их солей | |
CA2436265A1 (en) | 3-(3-amidinophenyl)-5-[({[1-(1-iminoethyl)-4-piperidyl]methyl}amino)methyl]benzoic acid dihydrochloride and process for preparing the same | |
SU655307A3 (ru) | Способ получени производных гуанидинов или их солей | |
SU399120A1 (ru) | Способ получения индоанилинов | |
JPS6261966A (ja) | プロピオンアミジン誘導体類及びそれらの製造方法 | |
US3567778A (en) | Process for preparing nitrosalicyl-hydrazides | |
US3090785A (en) | New process for preparing acylated | |
SU791230A3 (ru) | Способ получени бетаина пиридилалкилсульфоновой кислоты | |
US3004060A (en) | 1-cyanoformimidic acid hydrazide | |
US2970148A (en) | 1-isonicotinyl-2-veratrylidene hydrazine | |
KR800001550B1 (ko) | 5-(4-히드록시페닐) 히단토인의 제조법 | |
SU514825A1 (ru) | Способ получени хлоргидрата 1-фенил1-циклогексил-3-(1,-пиперидино) -пропанола-1 | |
SU271410A1 (ru) | Способ получения 1-амидин-3-(замещенный фенил)-карбамида |