DE2803205A1 - Das lysinsalz der alpha-methyl-(2- isopropyl-5-indanyl)-essigsaeure, verfahren zu seiner herstellung und pharmazeutische mittel - Google Patents
Das lysinsalz der alpha-methyl-(2- isopropyl-5-indanyl)-essigsaeure, verfahren zu seiner herstellung und pharmazeutische mittelInfo
- Publication number
- DE2803205A1 DE2803205A1 DE19782803205 DE2803205A DE2803205A1 DE 2803205 A1 DE2803205 A1 DE 2803205A1 DE 19782803205 DE19782803205 DE 19782803205 DE 2803205 A DE2803205 A DE 2803205A DE 2803205 A1 DE2803205 A1 DE 2803205A1
- Authority
- DE
- Germany
- Prior art keywords
- isopropyl
- acetic acid
- methyl
- lysine
- indanyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000008177 pharmaceutical agent Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- RYDUZJFCKYTEHX-UHFFFAOYSA-N 2-(2-propan-2-yl-2,3-dihydro-1h-inden-5-yl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=C2CC(C(C)C)CC2=C1 RYDUZJFCKYTEHX-UHFFFAOYSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000004472 Lysine Substances 0.000 claims description 7
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000007903 gelatin capsule Substances 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000018977 lysine Nutrition 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- ILNXYDNETCRFNA-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;hypochlorous acid Chemical compound ClO.NCCCC[C@H](N)C(O)=O ILNXYDNETCRFNA-JEDNCBNOSA-N 0.000 description 1
- MRASYQFTHLLRCS-UHFFFAOYSA-N 2-(2-propan-2-yl-2,3-dihydro-1h-inden-5-yl)acetic acid Chemical compound C1=C(CC(O)=O)C=C2CC(C(C)C)CC2=C1 MRASYQFTHLLRCS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010060968 Arthritis infective Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000007982 barbital buffer Substances 0.000 description 1
- 229960000796 barbital sodium Drugs 0.000 description 1
- FTOAOBMCPZCFFF-UHFFFAOYSA-N barbitone sodium Natural products CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- RGHFKWPGWBFQLN-UHFFFAOYSA-M sodium;5,5-diethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CCC1(CC)C([O-])=NC(=O)NC1=O RGHFKWPGWBFQLN-UHFFFAOYSA-M 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
- C07C59/50—Mandelic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB422677 | 1977-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2803205A1 true DE2803205A1 (de) | 1978-08-03 |
Family
ID=9773125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782803205 Pending DE2803205A1 (de) | 1977-02-02 | 1978-01-25 | Das lysinsalz der alpha-methyl-(2- isopropyl-5-indanyl)-essigsaeure, verfahren zu seiner herstellung und pharmazeutische mittel |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5396313A (el) |
| AT (1) | ATA52878A (el) |
| AU (1) | AU3272178A (el) |
| BE (1) | BE862834A (el) |
| DD (1) | DD133940A5 (el) |
| DE (1) | DE2803205A1 (el) |
| DK (1) | DK47278A (el) |
| ES (1) | ES466481A1 (el) |
| FR (1) | FR2379511A1 (el) |
| GR (1) | GR62849B (el) |
| NL (1) | NL7801204A (el) |
| NO (1) | NO780197L (el) |
| PT (1) | PT67572B (el) |
| SE (1) | SE7801087L (el) |
| SU (1) | SU667130A3 (el) |
| ZA (1) | ZA78403B (el) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3328401A1 (de) * | 1983-08-05 | 1985-02-21 | Merckle GmbH, 7902 Blaubeuren | Injizierbare loesung zur behandlung von entzuendungen |
| EP0261565A1 (en) * | 1986-09-26 | 1988-03-30 | S.I.F.I. Società Industria Farmaceutica Italiana S.p.A. | Lysine salt of 4-diphenylacetic acid and its ophthalmic formulations |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH592598A5 (el) * | 1973-10-30 | 1977-10-31 | Hexachimie | |
| IT1059677B (it) * | 1974-03-22 | 1982-06-21 | Neopharmed Spa | Sale di lisina ad azione terapeutica |
-
1978
- 1978-01-09 FR FR7800450A patent/FR2379511A1/fr not_active Withdrawn
- 1978-01-12 BE BE2056598A patent/BE862834A/xx unknown
- 1978-01-19 NO NO780197A patent/NO780197L/no unknown
- 1978-01-23 GR GR55241A patent/GR62849B/el unknown
- 1978-01-23 ZA ZA00780403A patent/ZA78403B/xx unknown
- 1978-01-24 PT PT67572A patent/PT67572B/pt unknown
- 1978-01-25 DE DE19782803205 patent/DE2803205A1/de active Pending
- 1978-01-25 AT AT52878A patent/ATA52878A/de not_active IP Right Cessation
- 1978-01-25 AU AU32721/78A patent/AU3272178A/en active Pending
- 1978-01-27 JP JP818678A patent/JPS5396313A/ja active Pending
- 1978-01-30 ES ES466481A patent/ES466481A1/es not_active Expired
- 1978-01-30 SE SE7801087A patent/SE7801087L/xx unknown
- 1978-01-31 DD DD78203487A patent/DD133940A5/xx unknown
- 1978-02-01 SU SU782571854A patent/SU667130A3/ru active
- 1978-02-01 DK DK47278A patent/DK47278A/da unknown
- 1978-02-02 NL NL7801204A patent/NL7801204A/xx not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3328401A1 (de) * | 1983-08-05 | 1985-02-21 | Merckle GmbH, 7902 Blaubeuren | Injizierbare loesung zur behandlung von entzuendungen |
| EP0261565A1 (en) * | 1986-09-26 | 1988-03-30 | S.I.F.I. Società Industria Farmaceutica Italiana S.p.A. | Lysine salt of 4-diphenylacetic acid and its ophthalmic formulations |
Also Published As
| Publication number | Publication date |
|---|---|
| BE862834A (fr) | 1978-07-12 |
| SE7801087L (sv) | 1978-08-03 |
| NO780197L (no) | 1978-08-03 |
| ATA52878A (de) | 1979-02-15 |
| FR2379511A1 (fr) | 1978-09-01 |
| NL7801204A (nl) | 1978-08-04 |
| JPS5396313A (en) | 1978-08-23 |
| AU3272178A (en) | 1979-08-02 |
| PT67572B (fr) | 1979-06-20 |
| DD133940A5 (de) | 1979-01-31 |
| ES466481A1 (es) | 1979-06-01 |
| SU667130A3 (ru) | 1979-06-05 |
| GR62849B (en) | 1979-06-20 |
| ZA78403B (en) | 1979-01-31 |
| DK47278A (da) | 1978-08-03 |
| PT67572A (fr) | 1978-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |