FI66881C - Foerfarande foer framstaellning av nya syraadditionssalter av 16beta-mono-kvaternaera ammoniumderivat av 2beta,16beta-bis-piperidino-5alfa-androstan - Google Patents
Foerfarande foer framstaellning av nya syraadditionssalter av 16beta-mono-kvaternaera ammoniumderivat av 2beta,16beta-bis-piperidino-5alfa-androstan Download PDFInfo
- Publication number
- FI66881C FI66881C FI792745A FI792745A FI66881C FI 66881 C FI66881 C FI 66881C FI 792745 A FI792745 A FI 792745A FI 792745 A FI792745 A FI 792745A FI 66881 C FI66881 C FI 66881C
- Authority
- FI
- Finland
- Prior art keywords
- androstane
- 16beta
- bis
- mono
- dipiperidino
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 229940083122 ganglion-blocking antiandrenergic bisquaternary ammonium compound Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- -1 diesters ammonium compounds Chemical class 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000002232 neuromuscular Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 229950010765 pivalate Drugs 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000005605 isobutyric acids Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7835667 | 1978-09-05 | ||
| GB7835667 | 1978-09-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI792745A7 FI792745A7 (fi) | 1980-03-06 |
| FI66881B FI66881B (fi) | 1984-08-31 |
| FI66881C true FI66881C (fi) | 1984-12-10 |
Family
ID=10499453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI792745A FI66881C (fi) | 1978-09-05 | 1979-09-04 | Foerfarande foer framstaellning av nya syraadditionssalter av 16beta-mono-kvaternaera ammoniumderivat av 2beta,16beta-bis-piperidino-5alfa-androstan |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4237126A (https=) |
| EP (1) | EP0008824B1 (https=) |
| JP (1) | JPS5535098A (https=) |
| AR (1) | AR228728A1 (https=) |
| AT (1) | ATE921T1 (https=) |
| AU (1) | AU526270B2 (https=) |
| CA (1) | CA1134813A (https=) |
| DE (1) | DE2962627D1 (https=) |
| DK (1) | DK159119C (https=) |
| ES (1) | ES483894A1 (https=) |
| FI (1) | FI66881C (https=) |
| GR (1) | GR72520B (https=) |
| HU (1) | HU181847B (https=) |
| IE (1) | IE50376B1 (https=) |
| IL (1) | IL58080A (https=) |
| NO (1) | NO151367C (https=) |
| NZ (1) | NZ191462A (https=) |
| PH (1) | PH16041A (https=) |
| PT (1) | PT70126A (https=) |
| ZA (1) | ZA794371B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE50675B1 (en) * | 1979-12-12 | 1986-06-11 | Akzo Nv | Bis-and mono-quaternary ammonium derivatives of 2beta,16beta-dipiperidino-5alpha-androstanes,processes for their preparation and pharmaceutical preparations |
| IE53463B1 (en) * | 1981-06-15 | 1988-11-23 | Akzo Nv | Mono-and bisquaternary ammonium derivatives of 2 beta,16 beta-d-amino-5 alpha-androstane derivatives and pharmaceutical preparations containing same |
| GB8709565D0 (en) * | 1987-04-23 | 1987-05-28 | Akzo Nv | 2beta,16beta-diaminoandrostanes |
| US5238957A (en) * | 1988-07-07 | 1993-08-24 | Presidenza Del Consiglio Dei Ministri-Uffico Del Ministro Per Il Coordinamento Delle Iniziative Per La Ricerca Scientifica E Tecnologica | Esters of 2,2-dimethyl-cyclopropane-carboxylic acid |
| US5418226A (en) * | 1992-04-22 | 1995-05-23 | Akzo N.V. | Monoquaternary 2,16-bispiperidinylandrostane derivatives |
| HU210076B (en) * | 1992-11-02 | 1995-01-30 | Tuba | Process for producing androstane derivatives substituted with quaternisaeted amino group in 16-position and for producing pharmaceutical compositions containing them |
| GB9302455D0 (en) * | 1993-02-08 | 1993-03-24 | Lab Inpharm N V | Process for preparing a pharmaceutical preparation having neuromuscular blocking activity |
| US5767112A (en) * | 1994-10-21 | 1998-06-16 | Poli Industria Chimica, S.P.A. | Muscle relaxant pharmaceutical compositions |
| US5553456A (en) * | 1995-05-17 | 1996-09-10 | Ramco, Inc. | Clathrate freeze desalination apparatus and method |
| IT1277700B1 (it) * | 1995-12-22 | 1997-11-11 | Poli Ind Chimica Spa | Processo di preparazione di 2-beta, 16-beta-diamino 3-alfa, 17-beta- diacilossi 5-alfaandrostani, bloccanti neuromuscolari a struttura |
| HU0402017D0 (en) * | 2004-10-07 | 2004-12-28 | Richter Gedeon Vegyeszet | Environment-friend process for the synthesis of quaternary ammonio-steroids |
| WO2006038047A1 (en) * | 2004-10-07 | 2006-04-13 | Richter Gedeon Vegyészeti Gyár Rt. | Environment-friend process for the synthesis of quaternary ammonio-steroιds |
| WO2006113462A2 (en) * | 2005-04-15 | 2006-10-26 | Lyotropic Therapeutics, Inc. | Formulations of quaternary ammonium neuromuscular blocking agents |
| DE102005030423A1 (de) * | 2005-06-30 | 2007-01-04 | Inresa Arzneimittel Gmbh | Neue Formulierung für Vecuroniumbromid |
| ATE554769T1 (de) | 2006-12-06 | 2012-05-15 | Cornell Res Foundation Inc | Neuromuskuläre blocker mit mittlerer dauer und antagonisten advon |
| US8592451B2 (en) | 2009-03-17 | 2013-11-26 | Cornell University | Reversible nondepolarizing neuromuscular blockade agents and methods for their use |
| US9220700B2 (en) | 2009-08-19 | 2015-12-29 | Cornell University | Cysteine for physiological injection |
| WO2022078483A1 (zh) * | 2020-10-15 | 2022-04-21 | 江苏恩华络康药物研发有限公司 | 甾体季铵化合物及其制备方法、制剂和用途 |
| CN116925171B (zh) * | 2023-07-10 | 2025-06-27 | 时森海(杭州)医药科技有限公司 | 含环丙甲基甾体类季铵盐化合物、中间体及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1138605A (en) * | 1965-02-19 | 1969-01-01 | Organon Labor Ltd | Improvements in or relating to new 2-ß,16-ß-diamino-androstanes |
| GB1454749A (en) * | 1972-11-29 | 1976-11-03 | Akzo Nv | 2beta, 16beta-diamino-androstanes and their preparation |
| HU171166B (hu) * | 1975-07-15 | 1977-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh ehpoksi-androstanov |
| US4177190A (en) * | 1975-08-01 | 1979-12-04 | Richter Gedeon Vegyeszeti Gyar Rt. | Diamino-androstanes and a process for the preparation of the said compounds |
| HU172522B (hu) * | 1975-08-01 | 1978-09-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh 2beta, 16beta-diamino-androstana i ikh chetvertichnykh solej |
-
1979
- 1979-08-15 DE DE7979200452T patent/DE2962627D1/de not_active Expired
- 1979-08-15 AT AT79200452T patent/ATE921T1/de not_active IP Right Cessation
- 1979-08-15 EP EP79200452A patent/EP0008824B1/en not_active Expired
- 1979-08-20 IE IE1593/79A patent/IE50376B1/en not_active IP Right Cessation
- 1979-08-20 US US06/067,878 patent/US4237126A/en not_active Expired - Lifetime
- 1979-08-20 ZA ZA00794371A patent/ZA794371B/xx unknown
- 1979-08-20 IL IL58080A patent/IL58080A/xx unknown
- 1979-08-28 PT PT70126A patent/PT70126A/pt unknown
- 1979-08-28 AU AU50348/79A patent/AU526270B2/en not_active Expired
- 1979-08-29 DK DK361779A patent/DK159119C/da not_active IP Right Cessation
- 1979-08-29 NO NO792810A patent/NO151367C/no unknown
- 1979-09-03 PH PH22990A patent/PH16041A/en unknown
- 1979-09-03 NZ NZ191462A patent/NZ191462A/xx unknown
- 1979-09-03 GR GR59954A patent/GR72520B/el unknown
- 1979-09-04 AR AR277956A patent/AR228728A1/es active
- 1979-09-04 JP JP11347079A patent/JPS5535098A/ja active Granted
- 1979-09-04 HU HU79AO484A patent/HU181847B/hu unknown
- 1979-09-04 FI FI792745A patent/FI66881C/fi not_active IP Right Cessation
- 1979-09-04 ES ES483894A patent/ES483894A1/es not_active Expired
- 1979-09-05 CA CA000335227A patent/CA1134813A/en not_active Expired
-
1980
- 1980-10-07 US US06/194,942 patent/US4297351A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE921T1 (de) | 1982-05-15 |
| EP0008824A1 (en) | 1980-03-19 |
| IE50376B1 (en) | 1986-04-16 |
| GR72520B (https=) | 1983-11-16 |
| FI66881B (fi) | 1984-08-31 |
| NZ191462A (en) | 1982-03-16 |
| IL58080A0 (en) | 1979-12-30 |
| JPS6245879B2 (https=) | 1987-09-29 |
| AU526270B2 (en) | 1982-12-23 |
| NO151367C (no) | 1985-03-27 |
| US4297351A (en) | 1981-10-27 |
| US4237126A (en) | 1980-12-02 |
| DK361779A (da) | 1980-03-06 |
| NO792810L (no) | 1980-03-06 |
| CA1134813A (en) | 1982-11-02 |
| EP0008824B1 (en) | 1982-04-28 |
| DE2962627D1 (en) | 1982-06-09 |
| HU181847B (en) | 1983-11-28 |
| PH16041A (en) | 1983-06-02 |
| JPS5535098A (en) | 1980-03-11 |
| IL58080A (en) | 1982-12-31 |
| FI792745A7 (fi) | 1980-03-06 |
| PT70126A (en) | 1979-09-01 |
| AU5034879A (en) | 1980-03-13 |
| DK159119C (da) | 1991-03-11 |
| IE791593L (en) | 1980-03-05 |
| NO151367B (no) | 1984-12-17 |
| DK159119B (da) | 1990-09-03 |
| AR228728A1 (es) | 1983-04-15 |
| ZA794371B (en) | 1980-08-27 |
| ES483894A1 (es) | 1980-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI66881C (fi) | Foerfarande foer framstaellning av nya syraadditionssalter av 16beta-mono-kvaternaera ammoniumderivat av 2beta,16beta-bis-piperidino-5alfa-androstan | |
| Piper et al. | Stimulation of arachidonic acid metabolism and generation of thromboxane A2 by leukotrienes B4, C4 and D4 in guinea-pig lung in vitro | |
| HU196827B (en) | Process for producing steroid esters and liposomes comprising the same | |
| Shashoua et al. | . gamma.-Aminobutyric acid esters. I. Synthesis, brain uptake, and pharmacological studies of aliphatic and steroid esters of. gamma.-aminobutyric acid | |
| KR19990028543A (ko) | 시알릴-루이스 ｘ 및 시알릴-루이스 ａ의 유사체로서의 디글리코실화 1,2-디올 | |
| FI68621C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 5-cyanoprostacyklinderivat | |
| DE69410081T2 (de) | Zwischenprodukte für die Herstellung von Endothelinrezeptor-Antagonist-Triterpen-Derivaten | |
| US4272525A (en) | Derivatives of polyene macrolide antibiotics containing an amino sugar moiety, process for the preparation thereof, and pharmaceutical compositions containing them | |
| EP0541594B1 (de) | Cyclopentanderivate, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung | |
| DE3541933A1 (de) | Cholecalciferolderivate | |
| FI76324C (fi) | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara isokinolinderivat. | |
| US5250525A (en) | 4-oxo-azetidine-2-sulfonic acids and their salts, processes for the preparation thereof and their use | |
| FI66394B (fi) | Foerfarande foer framstaellning av nya biskvaternaera ammoniumderivat av 2beta,16beta-dipiperidino-5alfa-androstaner | |
| US4312882A (en) | Thienyoxy and furyl containing analogs of prostacyclin and their use as medicaments | |
| FI70218C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3-substituerade tetrahydropyrrolo/1,2-a/pyrimidiner | |
| DE2706490A1 (de) | Neue carbonsaeureester | |
| US4440764A (en) | Water soluble esters of steroid-oxazole and pharmaceutical compositions containing them | |
| EP0031426B1 (de) | 7-Oxo-PGI2-derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende pharmazeutische Präparate | |
| EP0284547B1 (de) | 6-Oxoprostaglandin-E-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel | |
| Brewster et al. | (5Z)-7-(2, 2-Dimethyl-4-phenyl-1, 3-dioxan-cis-5-yl) heptenoic acid: a specific thromboxane A2 receptor antagonist | |
| US4271155A (en) | Water soluble hydrazones of 3-formylrifamycin SV, antibacterial compositions thereof and method of use thereof | |
| US3972917A (en) | 11-Deoxy 15-methyl prostaglandin E1 | |
| US4011338A (en) | 15-methyl prostaglandin compounds having bronchodilating activity | |
| WO1991001302A1 (de) | 9-fluor-prostaglandin-derivate, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung | |
| ITMI940696A1 (it) | Derivati dell'acido fosfonico utili nel trattamento delle malattie car. iovascolari |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: AKZO N.V. |