CA1113006A - Medicament agissant comme inhibiteur de la prostaglandine-synthetase - Google Patents
Medicament agissant comme inhibiteur de la prostaglandine-synthetaseInfo
- Publication number
- CA1113006A CA1113006A CA318,817A CA318817A CA1113006A CA 1113006 A CA1113006 A CA 1113006A CA 318817 A CA318817 A CA 318817A CA 1113006 A CA1113006 A CA 1113006A
- Authority
- CA
- Canada
- Prior art keywords
- glycoside
- pgs
- preparation according
- glycosides
- compounds
- 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
Links
- 230000000694 effects Effects 0.000 title abstract description 13
- 239000003814 drug Substances 0.000 title abstract description 5
- 229940079593 drug Drugs 0.000 title 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 title 1
- 229930182470 glycoside Natural products 0.000 claims abstract description 21
- 150000002148 esters Chemical class 0.000 claims abstract description 12
- 239000003112 inhibitor Substances 0.000 claims abstract description 11
- -1 sterol glycosides Chemical class 0.000 claims abstract description 7
- 229930182558 Sterol Natural products 0.000 claims abstract description 6
- 235000003702 sterols Nutrition 0.000 claims abstract description 6
- 150000002338 glycosides Chemical class 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 11
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- UVLDESQWQRMYKD-UHFFFAOYSA-N Neobotogenin Natural products CC1C(C2(C(=O)CC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 UVLDESQWQRMYKD-UHFFFAOYSA-N 0.000 claims description 7
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims description 7
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 claims description 7
- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 claims description 6
- WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 claims description 6
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- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 claims description 5
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- QOLRLLFJMZLYQJ-LOBDNJQFSA-N Hecogenin Chemical compound O([C@@H]1[C@@H]([C@]2(C(=O)C[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 QOLRLLFJMZLYQJ-LOBDNJQFSA-N 0.000 claims description 5
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- RTMWIZOXNKJHRE-UHFFFAOYSA-N Tigogenin Natural products CC1COC2CC(C)(OC12)C3CCC4C5CCC6CC(O)CCC6(C)C5CCC34C RTMWIZOXNKJHRE-UHFFFAOYSA-N 0.000 claims description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 4
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims description 3
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims description 3
- GMBQZIIUCVWOCD-WWASVFFGSA-N Sarsapogenine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-WWASVFFGSA-N 0.000 claims description 3
- 150000003432 sterols Chemical class 0.000 claims description 3
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 claims description 2
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 claims description 2
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 claims description 2
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 claims description 2
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 claims description 2
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 claims description 2
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 claims description 2
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- 235000012000 cholesterol Nutrition 0.000 claims description 2
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003937 drug carrier Substances 0.000 claims description 2
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- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims description 2
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- HVYWMOMLDIMFJA-VEIPTCAHSA-N (3r,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical compound C1C=C2C[C@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-VEIPTCAHSA-N 0.000 claims 1
- MBZYKEVPFYHDOH-BQNIITSRSA-N 24,25-dihydrolanosterol Chemical compound C([C@@]12C)C[C@H](O)C(C)(C)[C@@H]1CCC1=C2CC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@]21C MBZYKEVPFYHDOH-BQNIITSRSA-N 0.000 claims 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772759171 DE2759171A1 (de) | 1977-12-31 | 1977-12-31 | Arzneimittel mit wirkung als prostaglandinsynthetaseninhibitor |
| DEP2759171 | 1977-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113006A true CA1113006A (fr) | 1981-11-24 |
Family
ID=6027873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA318,817A Expired CA1113006A (fr) | 1977-12-31 | 1978-12-29 | Medicament agissant comme inhibiteur de la prostaglandine-synthetase |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS54101436A (fr) |
| AR (1) | AR223334A1 (fr) |
| AU (1) | AU516933B2 (fr) |
| BE (1) | BE873222A (fr) |
| CA (1) | CA1113006A (fr) |
| CH (1) | CH637829A5 (fr) |
| DE (1) | DE2759171A1 (fr) |
| DK (1) | DK587778A (fr) |
| ES (1) | ES476443A1 (fr) |
| FR (1) | FR2425859A1 (fr) |
| GB (1) | GB2039217B (fr) |
| IL (1) | IL56345A (fr) |
| IT (1) | IT1109336B (fr) |
| LU (1) | LU80739A1 (fr) |
| NL (1) | NL7812656A (fr) |
| NZ (1) | NZ189297A (fr) |
| PT (1) | PT69012A (fr) |
| SE (1) | SE466683B (fr) |
| ZA (1) | ZA787399B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2926463A1 (de) * | 1978-07-05 | 1980-01-24 | Roecar Holdings Nv | Spiroketaline und ihre verwendung |
| JPS5874619A (ja) * | 1981-10-29 | 1983-05-06 | Nippon Shinyaku Co Ltd | リポソ−ム及びその製法 |
| CA1209912A (fr) | 1982-04-19 | 1986-08-19 | Siegfrid Drewes | Extrait de plantes de la famille des hypoxidacees pour le traitement du cancer |
| US4602003A (en) * | 1982-05-17 | 1986-07-22 | Medical Research Foundation Of Oregon | Synthetic compounds to inhibit intestinal absorption of cholesterol in the treatment of hypercholesterolemia |
| US4602005A (en) * | 1982-05-17 | 1986-07-22 | Medical Research Foundation Of Oregon | Tigogenin cellobioside for treating hypercholesterolemia and atherosclerosis |
| DE3401178A1 (de) * | 1984-01-14 | 1985-07-18 | Roecar Holdings (Netherlands Antilles) N.V., Willemstad, Curacao, Niederländische Antillen | Verwendung von phytosterolglykosiden zur behandlung erhoehter 5(6)(alpha)-epoxicholesterolspiegel |
| DE3416112A1 (de) * | 1984-04-30 | 1985-10-31 | Roecar Holdings (Netherlands Antilles) N.V., Willemstad, Curacao, Niederländische Antillen | Verwendung von sterolinen und spiroketalinen als lipoxygenaseregulatoren |
| US5166194A (en) * | 1988-09-01 | 1992-11-24 | Roecar Holdings | Transdermally applicable pharmaceutical preparations having a pharmaceutically usable glycoside content |
| DE3829643A1 (de) * | 1988-09-01 | 1990-03-15 | Roecar Holdings Nv | Phyto- und zoosterole und deren derivate mit verbesserter wasserloeslichkeit |
| DE3829641A1 (de) * | 1988-09-01 | 1990-03-15 | Roecar Holdings Nv | Transdermal anwendbare pharmazeutische zubereitungen mit sterolinen und/oder spiroketalinen |
| DE3829640C1 (fr) * | 1988-09-01 | 1990-04-26 | Roecar Holdings (Netherlands Antilles) N.V., Willemstad, Curacao, Niederlaendische Antillen, Nl | |
| DE3838716A1 (de) * | 1988-11-15 | 1990-05-17 | Kanoldt Arzneimittel Gmbh | Arzneimittelzubereitung aus esterderivaten des hecogenins und dessen verwendung zur behandlung von benigner prostatahyperplasie |
| US5502038A (en) * | 1993-06-21 | 1996-03-26 | Medical Research Foundation Of Oregon | Cholesterol sequestrant glycosides that inhibit intestinal cholesterol absorption |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE35018B1 (en) * | 1970-03-18 | 1975-10-15 | Liebenberg R W | Therapeutic agent |
| US3966918A (en) * | 1973-12-12 | 1976-06-29 | Nippon Shinyaku Co., Ltd. | Method of preparing aqueous solutions of sterol glycosides and their ester derivatives |
| JPS51118817A (en) * | 1975-04-08 | 1976-10-19 | Nippon Shinyaku Co Ltd | A process for preparing absorbable steroid glycoside pharmaceutical |
-
1977
- 1977-12-31 DE DE19772759171 patent/DE2759171A1/de active Granted
-
1978
- 1978-12-28 AR AR274988A patent/AR223334A1/es active
- 1978-12-28 ES ES476443A patent/ES476443A1/es not_active Expired
- 1978-12-28 ZA ZA787399A patent/ZA787399B/xx unknown
- 1978-12-29 GB GB7850259A patent/GB2039217B/en not_active Expired
- 1978-12-29 NL NL7812656A patent/NL7812656A/xx not_active Application Discontinuation
- 1978-12-29 CA CA318,817A patent/CA1113006A/fr not_active Expired
- 1978-12-29 JP JP16443078A patent/JPS54101436A/ja active Pending
- 1978-12-29 IL IL56345A patent/IL56345A/xx not_active IP Right Cessation
- 1978-12-29 BE BE192687A patent/BE873222A/fr not_active IP Right Cessation
- 1978-12-29 PT PT69012A patent/PT69012A/pt unknown
- 1978-12-29 LU LU80739A patent/LU80739A1/de unknown
- 1978-12-29 AU AU43024/78A patent/AU516933B2/en not_active Expired
- 1978-12-29 FR FR7836823A patent/FR2425859A1/fr active Granted
- 1978-12-29 SE SE7813443A patent/SE466683B/sv not_active IP Right Cessation
- 1978-12-29 DK DK587778A patent/DK587778A/da not_active Application Discontinuation
- 1978-12-29 CH CH1330878A patent/CH637829A5/de not_active IP Right Cessation
- 1978-12-29 IT IT52493/78A patent/IT1109336B/it active
-
1979
- 1979-01-04 NZ NZ189297A patent/NZ189297A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH637829A5 (de) | 1983-08-31 |
| IL56345A0 (en) | 1979-03-12 |
| ES476443A1 (es) | 1979-10-16 |
| ZA787399B (en) | 1980-01-30 |
| IT1109336B (it) | 1985-12-16 |
| DE2759171C2 (fr) | 1990-10-25 |
| SE466683B (sv) | 1992-03-23 |
| JPS54101436A (en) | 1979-08-10 |
| GB2039217A (en) | 1980-08-06 |
| SE7813443L (sv) | 1979-07-01 |
| PT69012A (pt) | 1979-01-01 |
| LU80739A1 (de) | 1980-01-22 |
| NL7812656A (nl) | 1979-07-03 |
| NZ189297A (en) | 1984-10-19 |
| DK587778A (da) | 1979-07-01 |
| GB2039217B (en) | 1982-08-04 |
| AU516933B2 (en) | 1981-07-02 |
| FR2425859A1 (fr) | 1979-12-14 |
| AU4302478A (en) | 1979-07-05 |
| FR2425859B1 (fr) | 1983-04-08 |
| IT7852493A0 (it) | 1978-12-29 |
| IL56345A (en) | 1984-11-30 |
| BE873222A (fr) | 1979-06-29 |
| DE2759171A1 (de) | 1979-07-12 |
| AR223334A1 (es) | 1981-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |