DE2410307C2 - 2-(2-Thioäthyl)-4-carboxy-thiazolidin-Derivate - Google Patents
2-(2-Thioäthyl)-4-carboxy-thiazolidin-DerivateInfo
- Publication number
- DE2410307C2 DE2410307C2 DE2410307A DE2410307A DE2410307C2 DE 2410307 C2 DE2410307 C2 DE 2410307C2 DE 2410307 A DE2410307 A DE 2410307A DE 2410307 A DE2410307 A DE 2410307A DE 2410307 C2 DE2410307 C2 DE 2410307C2
- Authority
- DE
- Germany
- Prior art keywords
- thiazolidine
- thioethyl
- carboxy
- cooh
- mol
- 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.)
- Expired
Links
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 206010036790 Productive cough Diseases 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 4
- -1 2- {carboxymethylmercapto-ethyl) -thiazolidine-4-carboxylic acid diisopropylamine salt Chemical compound 0.000 description 4
- 229960001305 cysteine hydrochloride Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000000510 mucolytic effect Effects 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 208000001953 Hypotension Diseases 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 208000021822 hypotensive Diseases 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 210000003802 sputum Anatomy 0.000 description 3
- 208000024794 sputum Diseases 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- JJVXHDTWVIPRBZ-VKHMYHEASA-N (2r)-2-[carboxy(methyl)amino]-3-sulfanylpropanoic acid Chemical compound OC(=O)N(C)[C@@H](CS)C(O)=O JJVXHDTWVIPRBZ-VKHMYHEASA-N 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical group CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002085 irritant Substances 0.000 description 2
- 231100000021 irritant Toxicity 0.000 description 2
- 230000003533 narcotic effect Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003548 thiazolidines Chemical class 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- XUKUSRQRTHWIQG-UHFFFAOYSA-N 2-[2-(carboxymethylsulfanyl)ethyl]-1,3-thiazolidine-4-carboxylic acid Chemical compound OC(=O)CSCCC1NC(C(O)=O)CS1 XUKUSRQRTHWIQG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241001092142 Molina Species 0.000 description 1
- 206010028347 Muscle twitching Diseases 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 206010044314 Tracheobronchitis Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000001483 arginine derivatives Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 210000001326 carotid sinus Anatomy 0.000 description 1
- OJYGBLRPYBAHRT-IPQSZEQASA-N chloralose Chemical compound O1[C@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-IPQSZEQASA-N 0.000 description 1
- 229950009941 chloralose Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960002433 cysteine Drugs 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- QPUSANCBJDDXSA-UHFFFAOYSA-N ethanethiol;sodium Chemical compound [Na].CCS QPUSANCBJDDXSA-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000003462 vein Anatomy 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7310266A FR2222087B1 (enrdf_load_stackoverflow) | 1973-03-22 | 1973-03-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2410307A1 DE2410307A1 (de) | 1974-09-26 |
| DE2410307C2 true DE2410307C2 (de) | 1981-11-19 |
Family
ID=9116684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2410307A Expired DE2410307C2 (de) | 1973-03-22 | 1974-03-05 | 2-(2-Thioäthyl)-4-carboxy-thiazolidin-Derivate |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5241262B2 (enrdf_load_stackoverflow) |
| BE (1) | BE812653A (enrdf_load_stackoverflow) |
| DE (1) | DE2410307C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2222087B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1452207A (enrdf_load_stackoverflow) |
| LU (1) | LU69677A1 (enrdf_load_stackoverflow) |
| NL (1) | NL165654C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3325677A1 (de) * | 1982-08-06 | 1984-02-09 | Salus Researches-Sarm s.p.a., Roma | Guajakol-n-acetyl-4-thiazolidin-carboxylat, verfahren zu seiner herstellung und die verbindung enthaltende pharmazeutische zubereitungen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR8266M (enrdf_load_stackoverflow) * | 1968-12-31 | 1970-10-26 |
-
1973
- 1973-03-22 FR FR7310266A patent/FR2222087B1/fr not_active Expired
-
1974
- 1974-03-05 DE DE2410307A patent/DE2410307C2/de not_active Expired
- 1974-03-13 GB GB1107874A patent/GB1452207A/en not_active Expired
- 1974-03-20 NL NL7403785.A patent/NL165654C/xx not_active IP Right Cessation
- 1974-03-21 LU LU69677A patent/LU69677A1/xx unknown
- 1974-03-21 BE BE142297A patent/BE812653A/xx not_active IP Right Cessation
- 1974-03-22 JP JP49032454A patent/JPS5241262B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3325677A1 (de) * | 1982-08-06 | 1984-02-09 | Salus Researches-Sarm s.p.a., Roma | Guajakol-n-acetyl-4-thiazolidin-carboxylat, verfahren zu seiner herstellung und die verbindung enthaltende pharmazeutische zubereitungen |
Also Published As
| Publication number | Publication date |
|---|---|
| BE812653A (fr) | 1974-09-23 |
| FR2222087A1 (enrdf_load_stackoverflow) | 1974-10-18 |
| NL165654C (nl) | 1981-05-15 |
| JPS5241262B2 (enrdf_load_stackoverflow) | 1977-10-17 |
| FR2222087B1 (enrdf_load_stackoverflow) | 1976-04-09 |
| DE2410307A1 (de) | 1974-09-26 |
| LU69677A1 (enrdf_load_stackoverflow) | 1974-10-17 |
| GB1452207A (en) | 1976-10-13 |
| JPS49126666A (enrdf_load_stackoverflow) | 1974-12-04 |
| NL165654B (nl) | 1980-12-15 |
| NL7403785A (enrdf_load_stackoverflow) | 1974-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |