IL43684A - N-propionyl-l-4-hydroxy-proline and salts thereof,a process for their preparation and pharmaceutical compositions containing them - Google Patents
N-propionyl-l-4-hydroxy-proline and salts thereof,a process for their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL43684A IL43684A IL43684A IL4368473A IL43684A IL 43684 A IL43684 A IL 43684A IL 43684 A IL43684 A IL 43684A IL 4368473 A IL4368473 A IL 4368473A IL 43684 A IL43684 A IL 43684A
- Authority
- IL
- Israel
- Prior art keywords
- propionyl
- pharmaceutical compositions
- hydroxyproline
- salts
- preparation
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 7
- 150000003839 salts Chemical class 0.000 title claims abstract 5
- 238000000034 method Methods 0.000 title claims 6
- 238000002360 preparation method Methods 0.000 title claims 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims abstract 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims abstract 3
- 239000011248 coating agent Substances 0.000 claims abstract 2
- 238000000576 coating method Methods 0.000 claims abstract 2
- 239000003937 drug carrier Substances 0.000 claims abstract 2
- 229960000991 ketoprofen Drugs 0.000 claims abstract 2
- 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 claims abstract 2
- LMINNBXUMGNKMM-UHFFFAOYSA-N metiazinic acid Chemical compound C1=C(CC(O)=O)C=C2N(C)C3=CC=CC=C3SC2=C1 LMINNBXUMGNKMM-UHFFFAOYSA-N 0.000 claims abstract 2
- 229950005798 metiazinic acid Drugs 0.000 claims abstract 2
- 229960002895 phenylbutazone Drugs 0.000 claims abstract 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- -1 amine salts Chemical class 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims 1
- 229960002591 hydroxyproline Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 abstract 2
- 230000007691 collagen metabolic process Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229960000905 indomethacin Drugs 0.000 abstract 1
- 230000000051 modifying effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
Abstract
1397675 Anti-inflammatory &c medicines RHONE-POULENC SA 22 Nov 1973 [23 Nov 1972] 54274/73 Heading A5B [Also in Division C2] Pharmaceutical compositions having anti-inflammatory and collagen metabolism modifying activity, for oral or parenteral administration, comprise N-propionyl-L-4-hydroxyproline or a pharmaceutically acceptable salt thereof, optionally in conjunction with another pharmacologically acceptable compound (e.g. a known anti-inflammatory agent such as phenylbutazone, indomethacin, metiazinic acid and ketoprofene), in association with a pharmaceutically acceptable carrier or coating.
[GB1397675A]
Claims (11)
1.· N-Propionyl-L-4-hydroxyproline and salts thereof.
2. Alkali metal, alkaline earth metal, ammonium and pharmaceutically-acceptable amine salts of N-propionyl-L-4-hydroxyp oline.
3. Process for the preparation of N-propionyl-L-4«*hydroxyproline which comprises reacting a mixture of propionic anhydride and propionic acid with L-4-hydroxyproline.
4. Process according to claim 3 in which the reaction is carried out at a temperature of from 25° to 80QC,
5. Process according to claim 3 or 4 followed by the step of converting by methods known per se N-propionyl-L-4-hydroxyproline into an alkali metal, alkaline earth metal, ammonium or amine salt.
6. Process for the preparation of -propionyl-L-4-hydroxyproline and salts thereof substantially as hereinbefore described with especial reference to Example 1.
7. Pharmaceutical compositions which comprise N-propionyl-L-4-hydroxyproline, or a pharmaceutically-acceptable salt thereof, in association with a pharmaceutically-acceptable carrier or coating.
8. Pharmaceutical compositions according to claim 7 which also include a known anti-inflammatory agent.
9. Pharmaceutical compositions according to claim 8 in which the known anti-inflammatory agent is phenylbutazone, indomethaci , metiazinic acid or ketoprofene.
10. , Pharmaceutical compositions according to claim 7, 8 or 9 substantially as hereinbefore described.
11. Pharmaceutical compositions according to claim 7 substantially as described in Sxample 2. Attoraey for Applicant*
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7241639A FR2207702B1 (en) | 1972-11-23 | 1972-11-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43684A0 IL43684A0 (en) | 1974-03-14 |
| IL43684A true IL43684A (en) | 1976-06-30 |
Family
ID=9107588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43684A IL43684A (en) | 1972-11-23 | 1973-11-22 | N-propionyl-l-4-hydroxy-proline and salts thereof,a process for their preparation and pharmaceutical compositions containing them |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS504066A (en) |
| AR (1) | AR199319A1 (en) |
| AU (1) | AU473116B2 (en) |
| BE (1) | BE807684A (en) |
| CA (1) | CA1001635A (en) |
| CH (1) | CH576958A5 (en) |
| DD (1) | DD107455A5 (en) |
| DE (1) | DE2358470A1 (en) |
| ES (1) | ES420780A1 (en) |
| FR (1) | FR2207702B1 (en) |
| GB (1) | GB1397675A (en) |
| HU (1) | HU166917B (en) |
| IL (1) | IL43684A (en) |
| LU (1) | LU68846A1 (en) |
| NL (1) | NL7315685A (en) |
| OA (1) | OA04505A (en) |
| SE (1) | SE382453B (en) |
| SU (1) | SU507225A3 (en) |
| ZA (1) | ZA738874B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1281288C (en) * | 1984-11-05 | 1991-03-12 | Wilhelm Hoerrmann | Tumor therapy |
| JPS63218621A (en) * | 1987-03-09 | 1988-09-12 | Kazuoki Tsuchiya | Composition for prevention and remedy of obesity |
| WO2006046690A1 (en) * | 2004-10-28 | 2006-05-04 | Kyowa Hakko Kogyo Co., Ltd. | Composition for oral cavity |
-
1972
- 1972-11-23 FR FR7241639A patent/FR2207702B1/fr not_active Expired
-
1973
- 1973-11-08 OA OA55056A patent/OA04505A/en unknown
- 1973-11-15 NL NL7315685A patent/NL7315685A/xx unknown
- 1973-11-21 DD DD174787*A patent/DD107455A5/xx unknown
- 1973-11-21 AU AU62771/73A patent/AU473116B2/en not_active Expired
- 1973-11-21 AR AR251096A patent/AR199319A1/en active
- 1973-11-21 JP JP48131160A patent/JPS504066A/ja active Pending
- 1973-11-21 ZA ZA738874A patent/ZA738874B/en unknown
- 1973-11-21 HU HURO760A patent/HU166917B/hu unknown
- 1973-11-22 SU SU1972265A patent/SU507225A3/en active
- 1973-11-22 IL IL43684A patent/IL43684A/en unknown
- 1973-11-22 CH CH1648973A patent/CH576958A5/xx not_active IP Right Cessation
- 1973-11-22 LU LU68846A patent/LU68846A1/xx unknown
- 1973-11-22 GB GB5427473A patent/GB1397675A/en not_active Expired
- 1973-11-22 SE SE7315836A patent/SE382453B/en unknown
- 1973-11-22 CA CA186,521A patent/CA1001635A/en not_active Expired
- 1973-11-22 BE BE138064A patent/BE807684A/en unknown
- 1973-11-23 ES ES420780A patent/ES420780A1/en not_active Expired
- 1973-11-23 DE DE2358470A patent/DE2358470A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SU507225A3 (en) | 1976-03-15 |
| CA1001635A (en) | 1976-12-14 |
| CH576958A5 (en) | 1976-06-30 |
| GB1397675A (en) | 1975-06-18 |
| AR199319A1 (en) | 1974-08-23 |
| JPS504066A (en) | 1975-01-16 |
| ZA738874B (en) | 1974-10-30 |
| IL43684A0 (en) | 1974-03-14 |
| OA04505A (en) | 1980-03-30 |
| DD107455A5 (en) | 1974-08-05 |
| ES420780A1 (en) | 1976-04-01 |
| AU473116B2 (en) | 1976-06-10 |
| NL7315685A (en) | 1974-05-27 |
| FR2207702B1 (en) | 1975-11-28 |
| AU6277173A (en) | 1975-05-22 |
| FR2207702A1 (en) | 1974-06-21 |
| DE2358470A1 (en) | 1974-05-30 |
| BE807684A (en) | 1974-05-22 |
| LU68846A1 (en) | 1974-06-21 |
| SE382453B (en) | 1976-02-02 |
| HU166917B (en) | 1975-06-28 |
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