DE2752720A1 - Substituierte aminosaeuren - Google Patents
Substituierte aminosaeurenInfo
- Publication number
- DE2752720A1 DE2752720A1 DE19772752720 DE2752720A DE2752720A1 DE 2752720 A1 DE2752720 A1 DE 2752720A1 DE 19772752720 DE19772752720 DE 19772752720 DE 2752720 A DE2752720 A DE 2752720A DE 2752720 A1 DE2752720 A1 DE 2752720A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- alkylene
- radical
- proline
- compounds according
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- 150000001413 amino acids Chemical class 0.000 title claims description 14
- -1 fhenylglycine Chemical compound 0.000 claims description 108
- 238000000034 method Methods 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000004472 Lysine Substances 0.000 claims description 14
- 229940024606 amino acid Drugs 0.000 claims description 13
- 235000001014 amino acid Nutrition 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 239000004471 Glycine Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 6
- 239000004473 Threonine Substances 0.000 claims description 6
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- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 5
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 5
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 5
- 229960001230 asparagine Drugs 0.000 claims description 5
- 235000013930 proline Nutrition 0.000 claims description 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 4
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 4
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 3
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 235000009697 arginine Nutrition 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- 235000018417 cysteine Nutrition 0.000 claims description 3
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
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- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 235000009582 asparagine Nutrition 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- 229930182817 methionine Natural products 0.000 claims description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
- 235000002374 tyrosine Nutrition 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- 235000014393 valine Nutrition 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229960002429 proline Drugs 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000000047 product Substances 0.000 description 31
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- 239000000203 mixture Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
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- 229930182821 L-proline Natural products 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 11
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- JHFBRMLJWPWYEX-UHFFFAOYSA-N 3-acetylsulfanyl-2-(acetylsulfanylmethyl)propanoic acid Chemical compound CC(=O)SCC(C(O)=O)CSC(C)=O JHFBRMLJWPWYEX-UHFFFAOYSA-N 0.000 description 8
- 239000004395 L-leucine Substances 0.000 description 8
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- HGGZUPWPOAKANF-UHFFFAOYSA-N s-[2-(acetylsulfanylmethyl)-3-chloro-3-oxopropyl] ethanethioate Chemical compound CC(=O)SCC(C(Cl)=O)CSC(C)=O HGGZUPWPOAKANF-UHFFFAOYSA-N 0.000 description 1
- UUNMTQQOMUGHHC-UHFFFAOYSA-N s-[3-chloro-2-(methylsulfanylmethyl)-3-oxopropyl] ethanethioate Chemical compound CSCC(C(Cl)=O)CSC(C)=O UUNMTQQOMUGHHC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/60—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
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- 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
-
- 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)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (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)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/747,280 US4116962A (en) | 1976-12-03 | 1976-12-03 | Pyrrolidine and piperidine-2-carboxylic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2752720A1 true DE2752720A1 (de) | 1978-06-08 |
Family
ID=25004419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772752720 Ceased DE2752720A1 (de) | 1976-12-03 | 1977-11-25 | Substituierte aminosaeuren |
Country Status (33)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0009898A1 (en) * | 1978-09-11 | 1980-04-16 | University Of Miami | Novel anti-hypertensive mercaptoacylamino acid derivatives, their preparation and use |
| JPS5718611A (en) * | 1980-03-05 | 1982-01-30 | Uni Maiami Za | Angiotensin converting enzyme inhibitor |
| DE3243369A1 (de) | 1982-11-24 | 1984-05-24 | Basf Ag, 6700 Ludwigshafen | Bis-(benzoylthio)-carbonsaeuren, ihre herstellung und verwendung zur herstellung von wirkstoffen |
| AT379589B (de) * | 1978-08-11 | 1986-01-27 | Squibb & Sons Inc | Verfahren zur herstellung von neuen aether- und thioaether-mercaptoacyl-prolinen |
| EP0384636A1 (en) * | 1989-02-21 | 1990-08-29 | FISONS plc | Pharmaceutically active compounds |
| EP0654043A4 (en) * | 1993-05-03 | 1997-07-16 | Mallinckrodt Medical Inc | PROCESS FOR PREPARING A PROTEIN MARKED BY A METAL RADIONUCLEIDE. |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4116962A (en) * | 1976-12-03 | 1978-09-26 | E. R. Squibb & Sons, Inc. | Pyrrolidine and piperidine-2-carboxylic acid derivatives |
| US4198517A (en) * | 1976-12-03 | 1980-04-15 | E. R. Squibb & Sons, Inc. | Histidine derivatives |
| US4284780A (en) * | 1977-01-17 | 1981-08-18 | E. R. Squibb & Sons, Inc. | Amino acid derivatives |
| US4284779A (en) * | 1977-01-17 | 1981-08-18 | E. R. Squibb & Sons, Inc. | Amino acid derivatives |
| US4113715A (en) * | 1977-01-17 | 1978-09-12 | E. R. Squibb & Sons, Inc. | Amino acid derivatives |
| US4241076A (en) * | 1978-02-21 | 1980-12-23 | E. R. Squibb & Sons, Inc. | Halogenated substituted mercaptoacylamino acids |
| JPS559058A (en) * | 1978-07-06 | 1980-01-22 | Dainippon Pharmaceut Co Ltd | 1-(3-mercapto-2-methylpropanoyl)prolyl amino acid derivative |
| US4179568A (en) * | 1978-07-31 | 1979-12-18 | E. R. Squibb & Sons, Inc. | (N-lower alkyl-3,5-dioxo-3-pyrrolidinyl)thioalkanoylpyrrolidine-and piperidine-carboxylic acid compounds |
| NZ190995A (en) * | 1978-09-05 | 1982-03-09 | American Cyanamid Co | Substituted omega propionyl or butyryl l-prolines and pharmaceutical compositions |
| NL7809120A (nl) * | 1978-09-07 | 1980-03-11 | Oce Andeno B V Grubbenvorsterw | Werkwijze voor de bereiding van proline-derivaten. |
| US4698355A (en) * | 1979-08-14 | 1987-10-06 | University Of Miami | Anti-hypertensive agents |
| US4690938A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
| ZA794723B (en) * | 1978-09-11 | 1980-08-27 | Univ Miami | Anti-hypertensive agents |
| US4698356A (en) * | 1979-08-14 | 1987-10-06 | University Of Miami | Anti-hypertensive agents |
| US4690939A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
| US4690940A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
| US4690937A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
| US4695577A (en) * | 1979-08-14 | 1987-09-22 | University Of Miami | Anti-hypertensive agents |
| US4311697A (en) * | 1978-12-22 | 1982-01-19 | E. R. Squibb & Sons, Inc. | Derivatives of mercaptoacyl prolines and pipecolic acids |
| US4217359A (en) * | 1979-01-15 | 1980-08-12 | E. R. Squibb & Sons, Inc. | Carbamate derivatives of mercaptoacyl hydroxy prolines |
| US4297282A (en) * | 1979-03-02 | 1981-10-27 | Sumitomo Chemical Company, Limited | Resolution of mercaptopropionic acids |
| US4329473A (en) * | 1979-06-01 | 1982-05-11 | Almquist Ronald G | Oxoalkanoic acid derivatives as inhibitors of angiotensin converting enzyme |
| US4549992A (en) * | 1979-07-13 | 1985-10-29 | Usv Pharmaceutical Corp. | Antihypertensive amides |
| US4256761A (en) * | 1979-07-13 | 1981-03-17 | Usv Pharmaceutical Corporation | Antihypertensive amides |
| US4595675A (en) * | 1979-09-19 | 1986-06-17 | Hoechst Aktiengesellschaft | Bicyclic α-iminocarboxylic acid compounds having hypotensive activity |
| US4291040A (en) * | 1979-10-22 | 1981-09-22 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of 4-disubstituted prolines and 4-substituted dehydroprolines |
| US4356182A (en) * | 1979-10-22 | 1982-10-26 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of 4-disubstituted prolines |
| US4330548A (en) * | 1980-01-14 | 1982-05-18 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of keto substituted pipecolic acid |
| US4296113A (en) * | 1980-01-14 | 1981-10-20 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of keto substituted proline and pipecolic acid |
| IT1144077B (it) * | 1980-01-29 | 1986-10-29 | Sigma Tau Ind Farmaceuti | Carnitinammidi di amminoacidi otticamente attivi e procedimento per la loro preparazione |
| US4321392A (en) * | 1980-02-06 | 1982-03-23 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of 4-oxazolidine-carboxylic acids |
| US4734420A (en) * | 1980-03-05 | 1988-03-29 | University Of Miami | Anti-hypertensive agents |
| US4690936A (en) * | 1980-03-05 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
| US4350704A (en) * | 1980-10-06 | 1982-09-21 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids |
| US4342690A (en) * | 1980-04-28 | 1982-08-03 | American Cyanamid Company | ω-Heteroaroyl(propionyl or butyryl)-L-prolines |
| US4299769A (en) * | 1980-04-28 | 1981-11-10 | American Cyanamid Company | ω-Heteroaroyl(propionyl or butyryl)-L-prolines |
| US4342689A (en) * | 1980-04-28 | 1982-08-03 | American Cyanamid Company | ω-Heteroaroyl(propionyl or butyryl)-L-prolines |
| US4342691A (en) * | 1980-04-28 | 1982-08-03 | American Cyanamid Company | ω-Heteroaroyl(propionyl or butyryl)-L-prolines |
| US4316905A (en) * | 1980-07-01 | 1982-02-23 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of various 4-substituted prolines |
| US4344949A (en) * | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| US4499287A (en) * | 1981-02-02 | 1985-02-12 | E. R. Squibb & Sons, Inc. | Certain-4-hydroxy-proline derivatives |
| US4456761A (en) * | 1981-02-02 | 1984-06-26 | E. R. Squibb & Sons, Inc. | 4-Substituted dehydroprolines |
| US4532342A (en) * | 1981-02-20 | 1985-07-30 | Warner-Lambert Company | N-substituted amino acids as intermediates in the preparation of acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| US4521607A (en) * | 1981-02-27 | 1985-06-04 | Takeda Chemical Industries, Ltd. | Chromanyl glycines |
| US4503043A (en) * | 1981-12-07 | 1985-03-05 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acids |
| US4442038A (en) * | 1982-09-17 | 1984-04-10 | Norwich Eaton Pharmaceuticals, Inc. | Converting enzyme inhibitors |
| JPS61502468A (ja) * | 1984-06-08 | 1986-10-30 | チバ・ガイギ−・アクチェンゲゼルシャフト | Ｎ−置換ブチルアミド誘導体 |
| US5096925A (en) * | 1984-06-08 | 1992-03-17 | Ciba-Geigy Corporation | N-substituted butyramide derivatives |
| EP0225292A3 (en) * | 1985-12-06 | 1988-11-30 | Ciba-Geigy Ag | Certain n-substituted butyramide derivatives |
| US5166212A (en) * | 1985-12-06 | 1992-11-24 | Ciba-Geigy Corporation | Certain n-substituted butyramide derivatives |
| US20070086958A1 (en) * | 2005-10-14 | 2007-04-19 | Medafor, Incorporated | Formation of medically useful gels comprising microporous particles and methods of use |
| US20070087061A1 (en) * | 2005-10-14 | 2007-04-19 | Medafor, Incorporated | Method and composition for creating and/or activating a platelet-rich gel by contact with a porous particulate material, for use in wound care, tissue adhesion, or as a matrix for delivery of therapeutic components |
| WO2016111310A1 (ja) * | 2015-01-06 | 2016-07-14 | 国立研究開発法人理化学研究所 | 新規アンジオテンシン変換酵素阻害剤 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2714119A (en) * | 1953-08-07 | 1955-07-26 | Sterling Drug Inc | Process for preparing amides of alphamercapto lower fatty acids |
| US3510504A (en) * | 1965-01-21 | 1970-05-05 | Lilly Co Eli | Adamantyloxycarbonyl derivatives of alpha-amino acids |
| US3624143A (en) * | 1968-05-10 | 1971-11-30 | Merck & Co Inc | Compounds of the class {62 -aralkylthio-substituted-{60 -amino acids |
| BE792042A (fr) * | 1971-11-30 | 1973-05-29 | Ciba Geigy | Procede de preparation de nouvelles alcenylene-amines substituees en 3 |
| US3971828A (en) * | 1972-10-03 | 1976-07-27 | Santen Pharmaceutical Co. Ltd. | N-(mercaptoacyl)aminoacids |
| US4046889A (en) * | 1976-02-13 | 1977-09-06 | E. R. Squibb & Sons, Inc. | Azetidine-2-carboxylic acid derivatives |
| US4053651A (en) * | 1976-05-10 | 1977-10-11 | E. R. Squibb & Sons, Inc. | Compounds and method for alleviating angiotensin related hypertension |
| US4116962A (en) * | 1976-12-03 | 1978-09-26 | E. R. Squibb & Sons, Inc. | Pyrrolidine and piperidine-2-carboxylic acid derivatives |
-
1976
- 1976-12-03 US US05/747,280 patent/US4116962A/en not_active Expired - Lifetime
-
1977
- 1977-10-31 CA CA289,839A patent/CA1080729A/en not_active Expired
- 1977-11-01 ZA ZA00776508A patent/ZA776508B/xx unknown
- 1977-11-02 NZ NZ185603A patent/NZ185603A/xx unknown
- 1977-11-03 IL IL53292A patent/IL53292A0/xx not_active IP Right Cessation
- 1977-11-09 AU AU30485/77A patent/AU513051B2/en not_active Expired
- 1977-11-14 GR GR54801A patent/GR72452B/el unknown
- 1977-11-15 PH PH20435A patent/PH13488A/en unknown
- 1977-11-16 NL NLAANVRAGE7712612,A patent/NL187163C/xx not_active IP Right Cessation
- 1977-11-22 GB GB48626/77A patent/GB1591229A/en not_active Expired
- 1977-11-24 IT IT51939/77A patent/IT1112112B/it active
- 1977-11-25 DE DE19772752720 patent/DE2752720A1/de not_active Ceased
- 1977-11-25 ES ES464463A patent/ES464463A1/es not_active Expired
- 1977-11-25 IE IE2396/77A patent/IE46264B1/en not_active IP Right Cessation
- 1977-11-28 CS CS777852A patent/CS199514B2/cs unknown
- 1977-11-29 FR FR7735939A patent/FR2372803A1/fr active Granted
- 1977-11-30 AR AR270202A patent/AR220525A1/es active
- 1977-11-30 AT AT0857477A patent/AT362780B/de not_active IP Right Cessation
- 1977-12-01 HU HU77SU959A patent/HU176021B/hu unknown
- 1977-12-01 RO RO7792274A patent/RO74877A/ro unknown
- 1977-12-01 FI FI773639A patent/FI68221C/fi not_active IP Right Cessation
- 1977-12-01 YU YU02838/77A patent/YU283877A/xx unknown
- 1977-12-02 PT PT67353A patent/PT67353B/pt unknown
- 1977-12-02 SU SU772549899A patent/SU731891A3/ru active
- 1977-12-02 SE SE7713721A patent/SE423994B/xx not_active IP Right Cessation
- 1977-12-02 CH CH1479977A patent/CH634830A5/de not_active IP Right Cessation
- 1977-12-02 BE BE183132A patent/BE861453A/xx not_active IP Right Cessation
- 1977-12-02 DD DD77202381A patent/DD134224A5/xx unknown
- 1977-12-02 NO NO774125A patent/NO774125L/no unknown
- 1977-12-02 DK DK539077A patent/DK539077A/da not_active Application Discontinuation
- 1977-12-03 EG EG667/77A patent/EG12981A/xx active
- 1977-12-03 JP JP14651777A patent/JPS5371014A/ja active Granted
-
1978
- 1978-03-24 US US05/889,768 patent/US4140864A/en not_active Expired - Lifetime
- 1978-03-24 US US05/889,769 patent/US4154936A/en not_active Expired - Lifetime
- 1978-12-05 PH PH21886A patent/PH14255A/en unknown
-
1982
- 1982-02-25 HK HK88/82A patent/HK8882A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts, Bd. 83, 1975, 143573 p * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT379589B (de) * | 1978-08-11 | 1986-01-27 | Squibb & Sons Inc | Verfahren zur herstellung von neuen aether- und thioaether-mercaptoacyl-prolinen |
| EP0009898A1 (en) * | 1978-09-11 | 1980-04-16 | University Of Miami | Novel anti-hypertensive mercaptoacylamino acid derivatives, their preparation and use |
| JPS5718611A (en) * | 1980-03-05 | 1982-01-30 | Uni Maiami Za | Angiotensin converting enzyme inhibitor |
| DE3243369A1 (de) | 1982-11-24 | 1984-05-24 | Basf Ag, 6700 Ludwigshafen | Bis-(benzoylthio)-carbonsaeuren, ihre herstellung und verwendung zur herstellung von wirkstoffen |
| EP0110225A1 (de) * | 1982-11-24 | 1984-06-13 | BASF Aktiengesellschaft | Bis-(benzoylthio)-carbonsäuren, ihre Herstellung und Verwendung zur Herstellung von Wirkstoffen |
| EP0384636A1 (en) * | 1989-02-21 | 1990-08-29 | FISONS plc | Pharmaceutically active compounds |
| EP0654043A4 (en) * | 1993-05-03 | 1997-07-16 | Mallinckrodt Medical Inc | PROCESS FOR PREPARING A PROTEIN MARKED BY A METAL RADIONUCLEIDE. |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C149/23 |
|
| 8131 | Rejection |