DE2354143A1 - Salze der n-acetyl-thiazolidin-4-carbonsaeure - Google Patents
Salze der n-acetyl-thiazolidin-4-carbonsaeureInfo
- Publication number
- DE2354143A1 DE2354143A1 DE19732354143 DE2354143A DE2354143A1 DE 2354143 A1 DE2354143 A1 DE 2354143A1 DE 19732354143 DE19732354143 DE 19732354143 DE 2354143 A DE2354143 A DE 2354143A DE 2354143 A1 DE2354143 A1 DE 2354143A1
- Authority
- DE
- Germany
- Prior art keywords
- acetyl
- thiazolidine
- base
- salt according
- salt
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 claims description 22
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 10
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 5
- 229960003237 betaine Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 239000004475 Arginine Substances 0.000 claims description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 4
- BPZAIOKOQDGVMQ-UHFFFAOYSA-N 1-(1,3-thiazolidin-3-yl)ethanone Chemical class CC(=O)N1CCSC1 BPZAIOKOQDGVMQ-UHFFFAOYSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960001231 choline Drugs 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 229960003104 ornithine Drugs 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000003248 quinolines Chemical group 0.000 claims description 2
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 229960003581 pyridoxal Drugs 0.000 claims 1
- 235000008164 pyridoxal Nutrition 0.000 claims 1
- 239000011674 pyridoxal Substances 0.000 claims 1
- 125000002050 pyridoxal group Chemical group 0.000 claims 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 235000008160 pyridoxine Nutrition 0.000 description 6
- 239000011677 pyridoxine Substances 0.000 description 6
- 229940011671 vitamin b6 Drugs 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 108010082126 Alanine transaminase Proteins 0.000 description 4
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 208000006454 hepatitis Diseases 0.000 description 4
- 231100000283 hepatitis Toxicity 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 235000016709 nutrition Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WXTBYSIPOKXCPM-UHFFFAOYSA-N 3-acetyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC(=O)N1CSCC1C(O)=O WXTBYSIPOKXCPM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 3
- 206010067125 Liver injury Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001483 arginine derivatives Chemical class 0.000 description 3
- 231100000234 hepatic damage Toxicity 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 230000008818 liver damage Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 2
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- JJEJHMHHLCERIA-UHFFFAOYSA-N 2-acetyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC(=O)C1NC(C(O)=O)CS1 JJEJHMHHLCERIA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- -1 Pyridoxy salt Chemical class 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- NJZRLXNBGZBREL-UHFFFAOYSA-N glycine betaine hydrate Chemical compound [OH-].C[N+](C)(C)CC(O)=O NJZRLXNBGZBREL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000007863 steatosis Effects 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7238873A FR2204411B1 (enrdf_load_stackoverflow) | 1972-11-02 | 1972-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2354143A1 true DE2354143A1 (de) | 1974-05-16 |
Family
ID=9106569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732354143 Pending DE2354143A1 (de) | 1972-11-02 | 1973-10-29 | Salze der n-acetyl-thiazolidin-4-carbonsaeure |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS49133511A (enrdf_load_stackoverflow) |
| BE (1) | BE805680A (enrdf_load_stackoverflow) |
| CH (1) | CH579545A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2354143A1 (enrdf_load_stackoverflow) |
| ES (1) | ES420149A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2204411B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1410138A (enrdf_load_stackoverflow) |
| LU (1) | LU68722A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7314404A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001978A1 (en) * | 1977-10-06 | 1979-05-30 | Santen Pharmaceutical Co., Ltd | A derivative of thiazolidine-4-carboxylic acid, method for the preparation and pharmaceutical compositions comprising the compound |
| EP0348541A1 (en) * | 1988-06-29 | 1990-01-03 | YASON S.r.l | N-carbethoxy-4-thiazolidine-carboxylic acid, process for its preparation and its use as medicament |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1210859B (it) * | 1982-03-01 | 1989-09-29 | Ausonia Farma Srl | Composto chemioterapico, procedimento per la sua preparazione e relative composizioni farmaceutiche. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7001927A (enrdf_load_stackoverflow) * | 1969-02-11 | 1970-08-13 | ||
| FR2034536A1 (en) * | 1969-02-11 | 1970-12-11 | Academia Republ Roman A | Thiazolidinecarboxylic acid-4derivs |
-
1972
- 1972-11-02 FR FR7238873A patent/FR2204411B1/fr not_active Expired
-
1973
- 1973-10-04 BE BE136361A patent/BE805680A/xx unknown
- 1973-10-19 CH CH1483573A patent/CH579545A5/xx not_active IP Right Cessation
- 1973-10-19 NL NL7314404A patent/NL7314404A/xx not_active Application Discontinuation
- 1973-10-29 DE DE19732354143 patent/DE2354143A1/de active Pending
- 1973-10-31 ES ES420149A patent/ES420149A1/es not_active Expired
- 1973-10-31 LU LU68722D patent/LU68722A1/xx unknown
- 1973-11-01 JP JP12391773A patent/JPS49133511A/ja active Pending
- 1973-11-02 GB GB5109373A patent/GB1410138A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001978A1 (en) * | 1977-10-06 | 1979-05-30 | Santen Pharmaceutical Co., Ltd | A derivative of thiazolidine-4-carboxylic acid, method for the preparation and pharmaceutical compositions comprising the compound |
| EP0348541A1 (en) * | 1988-06-29 | 1990-01-03 | YASON S.r.l | N-carbethoxy-4-thiazolidine-carboxylic acid, process for its preparation and its use as medicament |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7314404A (enrdf_load_stackoverflow) | 1974-05-06 |
| LU68722A1 (enrdf_load_stackoverflow) | 1974-01-08 |
| JPS49133511A (enrdf_load_stackoverflow) | 1974-12-21 |
| GB1410138A (en) | 1975-10-15 |
| ES420149A1 (es) | 1976-03-16 |
| BE805680A (fr) | 1974-02-01 |
| FR2204411A1 (enrdf_load_stackoverflow) | 1974-05-24 |
| FR2204411B1 (enrdf_load_stackoverflow) | 1976-03-05 |
| CH579545A5 (enrdf_load_stackoverflow) | 1976-09-15 |
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