DE69114005T2 - 4-[(Thiophen-2-carbonyl)oxy]pyrrolidin-2-carbonsäure, deren Herstellung und deren Verwendung als entzündungshemmendes und wundheilendes Mittel. - Google Patents
4-[(Thiophen-2-carbonyl)oxy]pyrrolidin-2-carbonsäure, deren Herstellung und deren Verwendung als entzündungshemmendes und wundheilendes Mittel.Info
- Publication number
- DE69114005T2 DE69114005T2 DE69114005T DE69114005T DE69114005T2 DE 69114005 T2 DE69114005 T2 DE 69114005T2 DE 69114005 T DE69114005 T DE 69114005T DE 69114005 T DE69114005 T DE 69114005T DE 69114005 T2 DE69114005 T2 DE 69114005T2
- Authority
- DE
- Germany
- Prior art keywords
- inflammatory
- preparation
- thiophene
- carbonyl
- carboxylic acid
- 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 - Fee Related
Links
- UALJSXIPZBZMGU-UHFFFAOYSA-N 4-(thiophene-2-carbonyloxy)pyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1OC(=O)C1=CC=CS1 UALJSXIPZBZMGU-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 4
- 239000002260 anti-inflammatory agent Substances 0.000 title description 2
- 239000003357 wound healing promoting agent Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 3
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 3
- 230000000083 anti-dystrophic effect Effects 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 5
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical group [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 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
- 229960002591 hydroxyproline Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PMMYEEVYMWASQN-BKLSDQPFSA-N 4-hydroxy-L-proline Chemical compound OC1C[NH2+][C@H](C([O-])=O)C1 PMMYEEVYMWASQN-BKLSDQPFSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000000185 Localized scleroderma Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229960005113 oxaceprol Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- BJLFISSMRHKMGA-UHFFFAOYSA-N tridec-3-enoic acid Chemical compound CCCCCCCCCC=CCC(O)=O BJLFISSMRHKMGA-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT02048390A IT1248669B (it) | 1990-05-30 | 1990-05-30 | Derivato di idrossiprolina, sua preparazione e composizioni farmaceutiche che lo contengono |
| PCT/EP1991/000622 WO1991018896A1 (en) | 1990-05-30 | 1991-04-02 | Hydroxyproline derivative, a process for the preparation thereof and pharmaceutical compositions containing it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69114005D1 DE69114005D1 (de) | 1995-11-23 |
| DE69114005T2 true DE69114005T2 (de) | 1996-06-05 |
Family
ID=11167627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69114005T Expired - Fee Related DE69114005T2 (de) | 1990-05-30 | 1991-04-02 | 4-[(Thiophen-2-carbonyl)oxy]pyrrolidin-2-carbonsäure, deren Herstellung und deren Verwendung als entzündungshemmendes und wundheilendes Mittel. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0532506B1 (enExample) |
| AT (1) | ATE129244T1 (enExample) |
| AU (1) | AU7586191A (enExample) |
| DE (1) | DE69114005T2 (enExample) |
| ES (1) | ES2079650T3 (enExample) |
| GR (1) | GR3018126T3 (enExample) |
| IT (1) | IT1248669B (enExample) |
| WO (1) | WO1991018896A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2698997A (en) * | 1996-04-16 | 1997-11-07 | Chephasaar Chem.-Pharm. Fabrik Gmbh | Agent for inhibiting leukocyte invasion of tissues |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795327C3 (de) * | 1967-09-14 | 1979-09-13 | S.A.R.L. Franco-Chimie, Paris | Verwendung von N-Acetyl-1-Hydroxyprolin |
| FR2152456B1 (enExample) * | 1971-09-16 | 1974-10-18 | Morelle Jean |
-
1990
- 1990-05-30 IT IT02048390A patent/IT1248669B/it active IP Right Grant
-
1991
- 1991-04-02 AT AT91907069T patent/ATE129244T1/de not_active IP Right Cessation
- 1991-04-02 DE DE69114005T patent/DE69114005T2/de not_active Expired - Fee Related
- 1991-04-02 ES ES91907069T patent/ES2079650T3/es not_active Expired - Lifetime
- 1991-04-02 EP EP91907069A patent/EP0532506B1/en not_active Expired - Lifetime
- 1991-04-02 WO PCT/EP1991/000622 patent/WO1991018896A1/en not_active Ceased
- 1991-04-02 AU AU75861/91A patent/AU7586191A/en not_active Abandoned
-
1995
- 1995-11-21 GR GR950403243T patent/GR3018126T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1991018896A1 (en) | 1991-12-12 |
| IT9020483A0 (enExample) | 1990-05-30 |
| DE69114005D1 (de) | 1995-11-23 |
| ES2079650T3 (es) | 1996-01-16 |
| IT1248669B (it) | 1995-01-26 |
| EP0532506B1 (en) | 1995-10-18 |
| ATE129244T1 (de) | 1995-11-15 |
| GR3018126T3 (en) | 1996-02-29 |
| AU7586191A (en) | 1991-12-31 |
| EP0532506A1 (en) | 1993-03-24 |
| IT9020483A1 (it) | 1991-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0153277B1 (de) | Neue Pleuromutilinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP0011237A1 (de) | Polyäther-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| DE3141586C2 (enExample) | ||
| DE10024939A1 (de) | Neue Diphenylmethanderivate für Arzneimittel | |
| EP0029247B1 (de) | Alkenyl-thienyl-alkancarbonsäuren und ihre Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE69108408T2 (de) | 4,5-dihydroxy und 4,5,8-trihydroxy-9,10-dioxo-2-anthracencarbonsäure-dikohlensäureester und urethane mit therapeutischer wirkung. | |
| DE2941288C2 (enExample) | ||
| DE69600225T2 (de) | N,N'-di(Aralkyl)N,N'-di(carboxyalkyl)alkylendiaminderivate, N-(Aralkyl)N'-(carboxyalkyl)N,N'-di(carboxyalkyl)alkylendiaminderivate und N,N"-di(Aralkyl)N,N',N"-tri(carboxyalkyl)dialkylentriaminderivate und ihre Verwendung in Pharmazie und Kosmetik | |
| DE69114005T2 (de) | 4-[(Thiophen-2-carbonyl)oxy]pyrrolidin-2-carbonsäure, deren Herstellung und deren Verwendung als entzündungshemmendes und wundheilendes Mittel. | |
| DE69014930T2 (de) | Aralkylamin-Verbindungen. | |
| DE69208464T2 (de) | N-((4,5-dihydroxy- und 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracen-yl)carbonyl)aminosäure zur therapie osteoartikulärer leiden | |
| EP0033095B1 (de) | 5-Amino-tetrazol-Derivate von Retinsäuren, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| EP0009777B1 (de) | Retinsäure- und 7,8-Dehydro-retinsäure-N-(carboxy)-phenyl-amide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE2128375A1 (de) | Neue basische (Substituiert-alkyliden)amino-oxyalkylcarbonsäureester | |
| DE69007422T2 (de) | 1-(4-Aminophenyl)-2-piperidinopropanon-Derivate, Verfahren zu deren Herstellung und therapeutische Verwendung. | |
| EP0301371B1 (de) | Basisch substituierte Benzofurancarbonsäureamide, Verfahren zu ihrer Herstellung und sie enthaltende therapeutische Mittel | |
| DE69010169T2 (de) | Kristallines Magnesiumvalproat und Verfahren zu seiner Herstellung. | |
| EP0360784A1 (de) | Thienyloxy-alkylamin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2336671A1 (de) | Oxyessigsaeureaether von o-thymotinsaeureestern | |
| DE214357T1 (de) | Chemische verbindung mit antimykotischer, vernarbungsfoerdernder und entzuendungshemmender wirkung. | |
| EP0007347B1 (de) | Lipidsenkende Alkylenglykolderivate und Verfahren zu ihrer Herstellung | |
| EP0498011B1 (de) | Neue Salze der 2-(2,6-Dichloranilino)-phenylessigsäure, Verfahren zu ihrer Herstellung und ihre Verwendung für topisch anwendbare pharmazeutische Zubereitungen | |
| DE3214081C2 (enExample) | ||
| DE2735051A1 (de) | 4-phenylpiperidine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2740852A1 (de) | Basische 1-acylindol-3-acetocyessigsaeureester, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |