SE434943B - 4-tiazolidinkarboxylsyra - Google Patents
4-tiazolidinkarboxylsyraInfo
- Publication number
- SE434943B SE434943B SE7902910A SE7902910A SE434943B SE 434943 B SE434943 B SE 434943B SE 7902910 A SE7902910 A SE 7902910A SE 7902910 A SE7902910 A SE 7902910A SE 434943 B SE434943 B SE 434943B
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxy
- substituted
- methoxyphenyl
- mercapto
- thienyl
- Prior art date
Links
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 51
- -1 benzoyloxy, benzyloxycarbonyloxy, amino Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000012360 testing method Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 101800000734 Angiotensin-1 Proteins 0.000 description 13
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- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 12
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 12
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- 230000000694 effects Effects 0.000 description 12
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- 239000008101 lactose Substances 0.000 description 10
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- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
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- ZUDFHYZUQCNUJF-DSEUIKHZSA-N (4r)-2-thiophen-2-yl-1,3-thiazolidine-4-carboxylic acid Chemical compound N1[C@H](C(=O)O)CSC1C1=CC=CS1 ZUDFHYZUQCNUJF-DSEUIKHZSA-N 0.000 description 2
- IBLDDOBXWLJSEZ-BUSXIPJBSA-N (4r)-3-(3-benzoylsulfanylpropanoyl)-2-(2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid Chemical compound C([C@H]1C(=O)O)SC(C=2C(=CC=CC=2)O)N1C(=O)CCSC(=O)C1=CC=CC=C1 IBLDDOBXWLJSEZ-BUSXIPJBSA-N 0.000 description 2
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- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940127113 compound 57 Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000005332 diethylamines Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229960002474 hydralazine Drugs 0.000 description 1
- DMDGGSIALPNSEE-UHFFFAOYSA-N hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 description 1
- 229960003313 hydroflumethiazide Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 210000003692 ilium Anatomy 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 229940080435 lactose 250 mg Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- LKFCPWBGBPJDRC-UHFFFAOYSA-M potassium;thiobenzate Chemical compound [K+].[O-]C(=S)C1=CC=CC=C1 LKFCPWBGBPJDRC-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- TUJAHMBTEMTOMQ-UHFFFAOYSA-N s-(3-chloro-3-oxopropyl) benzenecarbothioate Chemical compound ClC(=O)CCSC(=O)C1=CC=CC=C1 TUJAHMBTEMTOMQ-UHFFFAOYSA-N 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000005303 weighing 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)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4163278A JPS54135768A (en) | 1978-04-08 | 1978-04-08 | Thiazolidine derivative |
| JP4965778A JPS54148783A (en) | 1978-04-25 | 1978-04-25 | Thiazolidine derivative |
| JP8111678A JPS557255A (en) | 1978-07-03 | 1978-07-03 | Thiazolidine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7902910L SE7902910L (sv) | 1979-10-09 |
| SE434943B true SE434943B (sv) | 1984-08-27 |
Family
ID=27290900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7902910A SE434943B (sv) | 1978-04-08 | 1979-04-02 | 4-tiazolidinkarboxylsyra |
Country Status (11)
| Country | Link |
|---|---|
| US (5) | US4430344A (show.php) |
| AU (1) | AU528115B2 (show.php) |
| CA (1) | CA1127157A (show.php) |
| CH (1) | CH649293A5 (show.php) |
| DE (1) | DE2914059C2 (show.php) |
| ES (1) | ES479410A1 (show.php) |
| FR (1) | FR2421889A1 (show.php) |
| GB (1) | GB2018248B (show.php) |
| IT (1) | IT1115158B (show.php) |
| NL (1) | NL7902710A (show.php) |
| SE (1) | SE434943B (show.php) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA794723B (en) * | 1978-09-11 | 1980-08-27 | Univ Miami | Anti-hypertensive agents |
| US4483861A (en) * | 1978-10-31 | 1984-11-20 | Santen Pharmaceutical Co., Ltd. | Antihypertensive sulfur-containing compounds |
| JPS56139455A (en) | 1980-04-02 | 1981-10-30 | Santen Pharmaceut Co Ltd | Sulfur-containing acylaminoacid |
| JPS5756425A (en) * | 1980-09-20 | 1982-04-05 | Santen Pharmaceut Co Ltd | Hypotensor |
| DE3152643A1 (de) * | 1980-12-29 | 1982-12-16 | Santen Pharmaceutical Co Ltd | Heterocyclic 5-membered ring compounds |
| JPS57112381A (en) * | 1980-12-29 | 1982-07-13 | Santen Pharmaceut Co Ltd | Five-membered heterocyclic compound |
| JPS57142962A (en) * | 1981-02-28 | 1982-09-03 | Santen Pharmaceut Co Ltd | Cyclodextrin clathrate compound of sulfur-containing compound |
| DE3134933A1 (de) * | 1981-09-03 | 1983-03-31 | Hoechst Ag, 6230 Frankfurt | "harnstoffderivate, verfahren zu ihrer herstellung und diese enthaltende medikamente sowie deren verwendung" |
| IT1153963B (it) * | 1982-03-22 | 1987-01-21 | Montedison Spa | Derivati dell'acido 2 0 4-tiazolidin-carbossilico 3-acil sostituiti ad azione fitoregolatrice e biostimolanti |
| IT1191109B (it) * | 1982-12-03 | 1988-02-24 | Simes | Derivati di acidi aminopiridincarbossilici,loro metodo di sintesi e composizioni farmaceutiche che li contengono |
| US4631343A (en) * | 1983-11-07 | 1986-12-23 | Eli Lilly And Company | Cyanopyrazole intermediates |
| GB2164333B (en) * | 1984-07-27 | 1988-11-16 | Boehringer Biochemia Srl | Antitussive and mucus regulating 2-substituted thiazolidines |
| IT1196485B (it) * | 1986-07-14 | 1988-11-16 | Zambon Spa | Derivati dell'acido tiazolidin-4-carbossilico ad attivita' farmaceutica |
| CN1030415A (zh) * | 1987-02-20 | 1989-01-18 | 山之内制药株式会社 | 饱和的杂环碳酰胺衍生物和它的制备方法 |
| IT1241415B (it) * | 1990-03-05 | 1994-01-14 | Yason Srl | Derivato dell'acido s-(2-tenoil)-tiolattico ad attivita' farmacologica |
| CA2178130C (en) * | 1995-06-05 | 2002-04-02 | Hiroshi Ikawa | Method of producing 2-naphthamide derivative, and compounds for producing 2-naphthamide derivative |
| US6083966A (en) | 1998-08-31 | 2000-07-04 | University Of Florida | Thiazoline acid derivatives |
| CN1585639A (zh) * | 1998-09-21 | 2005-02-23 | 佛罗里达大学研究基金会 | 抗疟疾制剂 |
| US20040044220A1 (en) * | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| WO2004017959A2 (en) * | 2002-08-22 | 2004-03-04 | University Of Florida | Antioxidant and radical scavenging activity of synthetic analogs of desferrithiocin |
| US7687468B2 (en) * | 2003-05-14 | 2010-03-30 | Viacell, LLC. | Rejuvenation of stored blood |
| AU2003270473A1 (en) * | 2003-09-09 | 2005-04-27 | University Of Florida | Desferrithiocin derivatives and their use as iron chelators |
| BRPI0610644B8 (pt) * | 2005-04-04 | 2021-05-25 | Univ Florida | composto e composição farmacêutica que compreende tal composto e um veículo ou diluente farmaceuticamente aceitável. |
| NZ579994A (en) | 2007-03-15 | 2011-09-30 | Univ Florida | Desferrithiocin polyether analogues useful in the treatment of pathological conditions responsive to chelation or sequestration of trivalent metal |
| EP2790697B1 (en) | 2011-12-16 | 2019-10-23 | University of Florida Research Foundation, Inc. | Uses of 4'-desferrithiocin analogs |
| RU2526619C2 (ru) * | 2012-12-12 | 2014-08-27 | Федеральное государственное бюджетное учреждение науки Институт высокомолекулярных соединений Российской академии наук | Способ получения (2r,4r)-2-алкил-3-(2-меркаптобензоил)-1,3-тиазолидин-4-карбоновых кислот |
| WO2015077655A1 (en) | 2013-11-22 | 2015-05-28 | University Of Florida Research Foundation, Inc. | Desferrithiocin analogs and uses thereof |
| WO2016176343A1 (en) | 2015-04-27 | 2016-11-03 | University Of Florida Research Foundation, Incorporated | Metabolically programmed metal chelators and uses thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3592905A (en) * | 1969-10-30 | 1971-07-13 | Merck & Co Inc | Therapeutic methods |
| FR2356423A1 (fr) * | 1976-07-01 | 1978-01-27 | Oeriu Simion | Derives de l'acide thiazolidinecarboxylique, leur preparation et leur application comme medicaments |
| AU518147B2 (en) * | 1976-12-03 | 1981-09-17 | E.R. Squibb & Sons, Inc. | Derivatives of thiazolidine, thiazine and morpholine carboxylic acids |
| US4192878A (en) | 1976-12-03 | 1980-03-11 | E. R. Squibb & Sons, Inc. | Derivatives of thiazolidinecarboxylic acids and related acids |
| JPS5834474B2 (ja) | 1977-06-29 | 1983-07-27 | ウェルファイド株式会社 | チアゾリジン誘導体の製造法 |
| JPS6047264B2 (ja) * | 1977-08-15 | 1985-10-21 | ウェルファイド株式会社 | チアゾリジン誘導体 |
| FR2395998A1 (fr) | 1977-06-29 | 1979-01-26 | Yoshitomi Pharmaceutical | Nouveaux derives de la thiazolidine et leur application dans le traitement de l'hypertension |
| FR2404635A1 (fr) * | 1977-09-28 | 1979-04-27 | Science Union & Cie | Nouveaux thioproprionylamides, leurs procedures d'obtention et leur emploi en therapeutique |
| US4282235A (en) * | 1978-05-22 | 1981-08-04 | E. R. Squibb & Sons, Inc. | Derivatives of thiazolidinecarboxylic acids and related acids |
| US4347371A (en) * | 1978-12-30 | 1982-08-31 | Santen Pharmaceutical Co., Ltd. | Disulfide compounds |
| US4374249A (en) * | 1980-12-23 | 1983-02-15 | American Cyanamid Company | [4R]-3-(ω-Aroylpropionyl)-4-thiazolidinecarboxylic acids and esters |
-
1979
- 1979-03-23 US US05/023,397 patent/US4430344A/en not_active Expired - Lifetime
- 1979-03-23 AU AU45444/79A patent/AU528115B2/en not_active Ceased
- 1979-04-02 SE SE7902910A patent/SE434943B/sv not_active IP Right Cessation
- 1979-04-03 GB GB7911642A patent/GB2018248B/en not_active Expired
- 1979-04-05 CH CH3226/79A patent/CH649293A5/de not_active IP Right Cessation
- 1979-04-06 DE DE2914059A patent/DE2914059C2/de not_active Expired
- 1979-04-06 NL NL7902710A patent/NL7902710A/xx not_active Application Discontinuation
- 1979-04-06 IT IT21666/79A patent/IT1115158B/it active
- 1979-04-06 ES ES479410A patent/ES479410A1/es not_active Expired
- 1979-04-06 CA CA325,022A patent/CA1127157A/en not_active Expired
- 1979-04-06 FR FR7908829A patent/FR2421889A1/fr active Granted
-
1981
- 1981-03-02 US US06/239,600 patent/US4423054A/en not_active Expired - Fee Related
- 1981-03-02 US US06/239,599 patent/US4457935A/en not_active Expired - Fee Related
- 1981-03-02 US US06/239,602 patent/US4356183A/en not_active Expired - Fee Related
- 1981-03-02 US US06/239,601 patent/US4386096A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4423054A (en) | 1983-12-27 |
| ES479410A1 (es) | 1980-08-16 |
| US4457935A (en) | 1984-07-03 |
| US4356183A (en) | 1982-10-26 |
| DE2914059A1 (de) | 1979-10-25 |
| FR2421889A1 (fr) | 1979-11-02 |
| AU4544479A (en) | 1979-10-18 |
| DE2914059C2 (de) | 1984-09-06 |
| FR2421889B1 (show.php) | 1982-11-19 |
| IT1115158B (it) | 1986-02-03 |
| US4430344A (en) | 1984-02-07 |
| CH649293A5 (de) | 1985-05-15 |
| AU528115B2 (en) | 1983-04-14 |
| SE7902910L (sv) | 1979-10-09 |
| NL7902710A (nl) | 1979-10-10 |
| GB2018248A (en) | 1979-10-17 |
| IT7921666A0 (it) | 1979-04-06 |
| CA1127157A (en) | 1982-07-06 |
| US4386096A (en) | 1983-05-31 |
| GB2018248B (en) | 1982-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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