IT1274020B - New salts of enantiomeric form of ketoprofen with TRIS, lysine, L-arginine etc. - with S-isomer used for chronic inflammatory conditions and R-isomer for analgesia - Google Patents
New salts of enantiomeric form of ketoprofen with TRIS, lysine, L-arginine etc. - with S-isomer used for chronic inflammatory conditions and R-isomer for analgesiaInfo
- Publication number
- IT1274020B IT1274020B ITMI940348A IT1274020B IT 1274020 B IT1274020 B IT 1274020B IT MI940348 A ITMI940348 A IT MI940348A IT 1274020 B IT1274020 B IT 1274020B
- Authority
- IT
- Italy
- Prior art keywords
- isomer
- ketoprofen
- tris
- lysine
- analgesia
- Prior art date
Links
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 title abstract 3
- 229960000991 ketoprofen Drugs 0.000 title abstract 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 title abstract 2
- 229930064664 L-arginine Natural products 0.000 title abstract 2
- 235000014852 L-arginine Nutrition 0.000 title abstract 2
- 230000036592 analgesia Effects 0.000 title abstract 2
- 230000001684 chronic effect Effects 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 2
- 239000004472 Lysine Substances 0.000 title 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 title 1
- 239000007983 Tris buffer Substances 0.000 title 1
- 230000004968 inflammatory condition Effects 0.000 title 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 abstract 2
- DKYWVDODHFEZIM-LLVKDONJSA-N (2r)-2-(3-benzoylphenyl)propanoic acid Chemical compound OC(=O)[C@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-LLVKDONJSA-N 0.000 abstract 1
- PTVWPYVOOKLBCG-CYBMUJFWSA-N (2r)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol Chemical compound C1CN(C[C@@H](O)CO)CCN1C1=CC=CC=C1 PTVWPYVOOKLBCG-CYBMUJFWSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 208000004998 Abdominal Pain Diseases 0.000 abstract 1
- 208000002881 Colic Diseases 0.000 abstract 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 abstract 1
- 208000025747 Rheumatic disease Diseases 0.000 abstract 1
- 206010070834 Sensitisation Diseases 0.000 abstract 1
- 230000001154 acute effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229960004722 dropropizine Drugs 0.000 abstract 1
- 230000002440 hepatic effect Effects 0.000 abstract 1
- 208000014674 injury Diseases 0.000 abstract 1
- 230000007774 longterm Effects 0.000 abstract 1
- 210000001640 nerve ending Anatomy 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- 208000024891 symptom Diseases 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 230000008733 trauma Effects 0.000 abstract 1
- 230000001562 ulcerogenic effect Effects 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Enantiomeric salts of S(+)- and R(-)-2-(3-benzoylphenyl)propionic acid (ketoprofen) with tris-(hydroxymethyl)aminomethane (TRIS), L- or D-lysine, L-arginine or (S)- or (R)-3-(4-phenylpiperazin-1-yl)propane- 1,2-diol (dextro- or laevo- dropropizine) are new. The enantiomers of ketoprofen have differing actions and clinical profiles. Only the S(+) form inhibits prostaglandin synthesis and has antiinflammatory activity (and is also ulcerogenic). This isomer is most useful in chronic rheumatic disorders requiring long-term, continuous or high dosage. The R(-) form is most useful for acute symptoms (renal, biliary or hepatic colic), trauma or other sensitisation of nerve endings requiring analgesia.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000348 IT1274020B (en) | 1994-02-25 | 1994-02-25 | New salts of enantiomeric form of ketoprofen with TRIS, lysine, L-arginine etc. - with S-isomer used for chronic inflammatory conditions and R-isomer for analgesia |
| US08/513,842 US5808069A (en) | 1993-03-09 | 1994-03-07 | Salts of 2-(3-benzoylphenyl) propionic acid with organic bases and pharmaceutical compositions thereof |
| AU62905/94A AU6290594A (en) | 1993-03-09 | 1994-03-07 | Salts of 2-(3-benzoylphenyl)propionic acid with achiral and chiral organic bases and pharmaceutical compositions thereof |
| PCT/IT1994/000020 WO1994020449A1 (en) | 1993-03-09 | 1994-03-07 | Salts of 2-(3-benzoylphenyl)propionic acid with achiral and chiral organic bases and pharmaceutical compositions thereof |
| EP94910514A EP0703893A1 (en) | 1993-03-09 | 1994-03-07 | Salts of 2-(3-benzoylphenyl) propionic acid with achiral and chiral organic bases and pharmaceutical compositions thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000348 IT1274020B (en) | 1994-02-25 | 1994-02-25 | New salts of enantiomeric form of ketoprofen with TRIS, lysine, L-arginine etc. - with S-isomer used for chronic inflammatory conditions and R-isomer for analgesia |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| ITMI940348A0 ITMI940348A0 (en) | 1994-02-25 |
| ITMI940348A1 ITMI940348A1 (en) | 1995-08-26 |
| IT1274020B true IT1274020B (en) | 1997-07-14 |
Family
ID=11367990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT000348 IT1274020B (en) | 1993-03-09 | 1994-02-25 | New salts of enantiomeric form of ketoprofen with TRIS, lysine, L-arginine etc. - with S-isomer used for chronic inflammatory conditions and R-isomer for analgesia |
Country Status (1)
| Country | Link |
|---|---|
| IT (1) | IT1274020B (en) |
-
1994
- 1994-02-25 IT IT000348 patent/IT1274020B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI940348A0 (en) | 1994-02-25 |
| ITMI940348A1 (en) | 1995-08-26 |
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| 0001 | Granted |