IE48514B1 - Substituted amino acids,their use and production and pharmaceutical products containing same - Google Patents
Substituted amino acids,their use and production and pharmaceutical products containing sameInfo
- Publication number
- IE48514B1 IE48514B1 IE1129/79A IE112979A IE48514B1 IE 48514 B1 IE48514 B1 IE 48514B1 IE 1129/79 A IE1129/79 A IE 1129/79A IE 112979 A IE112979 A IE 112979A IE 48514 B1 IE48514 B1 IE 48514B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- signifies
- general formula
- acid
- cooh
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 20
- 229940127557 pharmaceutical product Drugs 0.000 title claims description 13
- 150000001413 amino acids Chemical class 0.000 title description 4
- 239000002253 acid Substances 0.000 claims abstract description 92
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 150000007513 acids Chemical class 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 31
- 230000008569 process Effects 0.000 claims abstract description 21
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- -1 biphenylyl Chemical class 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- 150000007529 inorganic bases Chemical class 0.000 claims description 27
- 150000007530 organic bases Chemical class 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- PIGVXRKGKGOZME-UHFFFAOYSA-N [C]1=C(C=CC=C1)C1=CC=CC=C1 Chemical compound [C]1=C(C=CC=C1)C1=CC=CC=C1 PIGVXRKGKGOZME-UHFFFAOYSA-N 0.000 claims description 3
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- 238000006243 chemical reaction Methods 0.000 description 16
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- 150000002148 esters Chemical class 0.000 description 14
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 14
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- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical compound NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 10
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- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 7
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- 239000000126 substance Substances 0.000 description 7
- 231100000397 ulcer Toxicity 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000010933 acylation Effects 0.000 description 6
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
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- VQZSWPBNFYGZNV-UHFFFAOYSA-N ethyl 4-(2-phenylanilino)butanoate Chemical compound CCOC(=O)CCCNC1=CC=CC=C1C1=CC=CC=C1 VQZSWPBNFYGZNV-UHFFFAOYSA-N 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- POGFKTXFRBWGJC-UHFFFAOYSA-N 4-(n-(4-chlorobenzoyl)-2-phenylanilino)butanoic acid Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1N(CCCC(=O)O)C(=O)C1=CC=C(Cl)C=C1 POGFKTXFRBWGJC-UHFFFAOYSA-N 0.000 description 4
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
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- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Soy Sauces And Products Related Thereto (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Saccharide Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH650478 | 1978-06-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE791129L IE791129L (en) | 1979-12-14 |
| IE48514B1 true IE48514B1 (en) | 1985-02-20 |
Family
ID=4310656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1129/79A IE48514B1 (en) | 1978-06-14 | 1979-08-08 | Substituted amino acids,their use and production and pharmaceutical products containing same |
Country Status (18)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3042482A1 (de) * | 1980-11-11 | 1982-06-24 | A. Nattermann & Cie GmbH, 5000 Köln | N-benzoyl- (omega) -anilinoalkancarbonsaeuren, -salze und -ester, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4440941A (en) * | 1980-12-22 | 1984-04-03 | Usv Pharmaceutical Corporation | Aroyl-aminoacids, amides and esters thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3697563A (en) * | 1970-06-29 | 1972-10-10 | Inst Chemioterapico Italiano S | (3,4,5-trimethoxy-benzamido)-alkanoic acids for prophylaxis and treatment of cardiac disorders |
-
1979
- 1979-06-12 PL PL21629279A patent/PL216292A1/xx unknown
- 1979-06-12 EP EP79101912A patent/EP0006218B1/de not_active Expired
- 1979-06-12 DE DE19792923731 patent/DE2923731A1/de not_active Withdrawn
- 1979-06-12 DE DE7979101912T patent/DE2962949D1/de not_active Expired
- 1979-06-12 PT PT69762A patent/PT69762A/pt unknown
- 1979-06-12 ES ES481492A patent/ES481492A1/es not_active Expired
- 1979-06-12 GR GR59321A patent/GR65292B/el unknown
- 1979-06-12 DK DK244979A patent/DK244979A/da not_active Application Discontinuation
- 1979-06-12 AT AT79101912T patent/ATE1093T1/de not_active IP Right Cessation
- 1979-06-12 FR FR7914946A patent/FR2432501A1/fr not_active Withdrawn
- 1979-06-12 AU AU47978/79A patent/AU525423B2/en not_active Ceased
- 1979-06-12 GB GB7920409A patent/GB2024813A/en not_active Withdrawn
- 1979-06-12 JP JP7315079A patent/JPS54163558A/ja active Pending
- 1979-06-12 BE BE6/46861A patent/BE876933A/xx unknown
- 1979-06-13 ZA ZA792943A patent/ZA792943B/xx unknown
- 1979-06-13 CA CA000329666A patent/CA1153387A/en not_active Expired
- 1979-06-13 IL IL57554A patent/IL57554A0/xx unknown
- 1979-06-14 NZ NZ190722A patent/NZ190722A/xx unknown
- 1979-08-08 IE IE1129/79A patent/IE48514B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2923731A1 (de) | 1980-01-03 |
| AU4797879A (en) | 1979-12-20 |
| IE791129L (en) | 1979-12-14 |
| BE876933A (fr) | 1979-12-12 |
| EP0006218B1 (de) | 1982-05-26 |
| DE2962949D1 (en) | 1982-07-15 |
| ZA792943B (en) | 1980-06-25 |
| AU525423B2 (en) | 1982-11-04 |
| GB2024813A (en) | 1980-01-16 |
| GR65292B (en) | 1980-08-01 |
| ATE1093T1 (de) | 1982-06-15 |
| CA1153387A (en) | 1983-09-06 |
| IL57554A0 (en) | 1979-10-31 |
| NZ190722A (en) | 1981-11-19 |
| JPS54163558A (en) | 1979-12-26 |
| PL216292A1 (enrdf_load_stackoverflow) | 1980-03-24 |
| PT69762A (de) | 1979-07-01 |
| ES481492A1 (es) | 1980-03-01 |
| EP0006218A1 (de) | 1980-01-09 |
| DK244979A (da) | 1979-12-15 |
| FR2432501A1 (fr) | 1980-02-29 |
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