NO128152B - - Google Patents
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- Publication number
- NO128152B NO128152B NO00162597A NO16259766A NO128152B NO 128152 B NO128152 B NO 128152B NO 00162597 A NO00162597 A NO 00162597A NO 16259766 A NO16259766 A NO 16259766A NO 128152 B NO128152 B NO 128152B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- steroid
- dione
- azide
- carbon atoms
- Prior art date
Links
- 239000002904 solvent Substances 0.000 claims description 11
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 150000003431 steroids Chemical group 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 150000003128 pregnanes Chemical class 0.000 claims description 4
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- -1 oxazoline compound Chemical class 0.000 description 2
- 230000001072 progestational effect Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PFKXNKHKMKLGCZ-UHFFFAOYSA-N 2-(2H-1,3-oxazol-3-yl)acetic acid Chemical compound O1CN(C=C1)CC(=O)O PFKXNKHKMKLGCZ-UHFFFAOYSA-N 0.000 description 1
- GINTUCRWMKSHSV-XNKUGNQISA-N 4,5-dihydro-1,3-oxazole;(8s,9s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CN=CO1.C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 GINTUCRWMKSHSV-XNKUGNQISA-N 0.000 description 1
- JWMFYGXQPXQEEM-UHFFFAOYSA-N 5alpha-Pregnan Natural products C1CC2CCCCC2(C)C2C1C1CCC(CC)C1(C)CC2 JWMFYGXQPXQEEM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- BLAKAEFIFWAFGH-UHFFFAOYSA-N acetyl acetate;pyridine Chemical compound C1=CC=NC=C1.CC(=O)OC(C)=O BLAKAEFIFWAFGH-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0027—Azides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/0025—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16
- C07J7/0035—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16 by a hydroxy group free esterified or etherified
-
- 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
- C07J71/001—Oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0057—Nitrogen and oxygen
- C07J71/0068—Nitrogen and oxygen at position 16(17)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Machines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17027/65A GB1077392A (en) | 1965-04-22 | 1965-04-22 | New steroids |
| GB3586565 | 1965-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128152B true NO128152B (xx) | 1973-10-08 |
Family
ID=26252388
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00162506A NO127346B (xx) | 1965-04-22 | 1966-04-06 | |
| NO00162597A NO128152B (xx) | 1965-04-22 | 1966-04-15 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00162506A NO127346B (xx) | 1965-04-22 | 1966-04-06 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US3436389A (xx) |
| AT (2) | AT260440B (xx) |
| BE (2) | BE679821A (xx) |
| BR (2) | BR6678805D0 (xx) |
| CH (2) | CH471833A (xx) |
| DE (3) | DE1568950A1 (xx) |
| DK (2) | DK116870B (xx) |
| ES (1) | ES325755A1 (xx) |
| FI (2) | FI44905C (xx) |
| FR (1) | FR5645M (xx) |
| GB (1) | GB1077392A (xx) |
| IL (2) | IL25494A (xx) |
| NL (3) | NL6605174A (xx) |
| NO (2) | NO127346B (xx) |
| SE (2) | SE323675B (xx) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1119081A (en) * | 1966-01-11 | 1968-07-10 | Lepetit Spa | New steroids |
| IT1141930B (it) * | 1980-04-28 | 1986-10-08 | Lepetit Spa | Esteri idrosolubili di steroido-ossazoli e loro composizioni farmaceutiche |
| IT1134455B (it) * | 1980-11-26 | 1986-08-13 | Lepetit Spa | Procedimento per la preparazione di derivati 16alfa-idrossi-17alfa-aminopregnanici |
| AR045536A1 (es) * | 2003-08-29 | 2005-11-02 | Ranbaxy Lab Ltd | Inhibidores de la fosfodiesterasa tipo -iv |
| EP1694655A2 (en) * | 2003-11-26 | 2006-08-30 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| US20080009535A1 (en) * | 2004-08-30 | 2008-01-10 | Sarala Balachandran | Inhibitors of phosphodiesterase type-IV |
| US7915286B2 (en) | 2005-09-16 | 2011-03-29 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| EP1948167A1 (en) * | 2005-10-19 | 2008-07-30 | Ranbaxy Laboratories, Ltd. | Compositions of phosphodiesterase type iv inhibitors |
| US20090221664A1 (en) | 2005-10-19 | 2009-09-03 | Abhijit Ray | Pharmaceutical compositions of muscarinic receptor antagonists |
| CA2664247A1 (en) * | 2006-09-22 | 2008-03-27 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-iv |
| WO2008035316A2 (en) * | 2006-09-22 | 2008-03-27 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| CN101177443B (zh) * | 2006-11-09 | 2011-08-03 | 天津药业研究院有限公司 | 新的甾体化合物及其应用 |
| US20080207659A1 (en) * | 2007-02-15 | 2008-08-28 | Asit Kumar Chakraborti | Inhibitors of phosphodiesterase type 4 |
| MX2009009793A (es) * | 2007-03-14 | 2009-10-16 | Ranbaxy Lab Ltd | Derivados de pirazolo (3,4-b) piridina como inhibidores de fosfodiesterasa. |
| US20110130403A1 (en) * | 2007-03-14 | 2011-06-02 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b] pyridine derivatives as phosphodiesterase inhibitors |
| EP2111861A1 (en) | 2008-04-21 | 2009-10-28 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type IV inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2874154A (en) * | 1954-10-15 | 1959-02-17 | Syntex Sa | Process for the production of 20-keto-21-iodo steroids |
| US2923721A (en) * | 1955-12-13 | 1960-02-02 | Lab Francais Chimiotherapie | Method of preparing 3-keto delta1, 4 steroids |
| DE1223376B (de) * | 1963-12-14 | 1966-08-25 | Hoechst Ag | Verfahren zur Herstellung von 17alpha-Cyan-16alpha-hydroxy-steroiden der Pregnanreihe |
| US3349084A (en) * | 1965-05-17 | 1967-10-24 | Upjohn Co | Steroidal [16, 17-d]-2'-isoxazolines of the pregnane series |
-
0
- NL NL128816D patent/NL128816C/xx active
-
1965
- 1965-04-22 GB GB17027/65A patent/GB1077392A/en not_active Expired
-
1966
- 1966-03-30 US US538574A patent/US3436389A/en not_active Expired - Lifetime
- 1966-03-30 US US538555A patent/US3413286A/en not_active Expired - Lifetime
- 1966-03-30 IL IL25494A patent/IL25494A/xx unknown
- 1966-03-30 IL IL25493A patent/IL25493A/en unknown
- 1966-04-06 NO NO00162506A patent/NO127346B/no unknown
- 1966-04-15 NO NO00162597A patent/NO128152B/no unknown
- 1966-04-16 FI FI660985A patent/FI44905C/fi active
- 1966-04-16 FI FI660986A patent/FI44906C/fi active
- 1966-04-18 NL NL6605174A patent/NL6605174A/xx unknown
- 1966-04-18 BR BR178805/66A patent/BR6678805D0/pt unknown
- 1966-04-20 DE DE19661568950 patent/DE1568950A1/de active Pending
- 1966-04-20 DE DE1793662A patent/DE1793662C3/de not_active Expired
- 1966-04-21 DE DE19661568951 patent/DE1568951A1/de active Pending
- 1966-04-21 BE BE679821A patent/BE679821A/xx not_active IP Right Cessation
- 1966-04-21 ES ES0325755A patent/ES325755A1/es not_active Expired
- 1966-04-21 SE SE5444/66A patent/SE323675B/xx unknown
- 1966-04-21 DK DK204266AA patent/DK116870B/da unknown
- 1966-04-21 SE SE5443/66A patent/SE323674B/xx unknown
- 1966-04-21 NL NL6605375A patent/NL6605375A/xx unknown
- 1966-04-21 BE BE679820D patent/BE679820A/xx not_active IP Right Cessation
- 1966-04-21 DK DK204166AA patent/DK117631B/da unknown
- 1966-04-22 AT AT382766A patent/AT260440B/de active
- 1966-04-22 CH CH584666A patent/CH471833A/fr not_active IP Right Cessation
- 1966-04-22 AT AT382266A patent/AT265539B/de active
- 1966-04-22 CH CH584766A patent/CH453351A/fr unknown
- 1966-05-18 BR BR179615/66A patent/BR6679615D0/pt unknown
- 1966-07-20 FR FR70013A patent/FR5645M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT265539B (de) | 1968-10-10 |
| CH453351A (fr) | 1968-06-14 |
| DK117631B (da) | 1970-05-19 |
| GB1077392A (en) | 1967-07-26 |
| FI44906C (fi) | 1972-02-10 |
| IL25494A (en) | 1970-03-22 |
| IL25493A (en) | 1969-12-31 |
| SE323675B (xx) | 1970-05-11 |
| DE1793662C3 (de) | 1973-11-08 |
| AT260440B (de) | 1968-03-11 |
| DK116870B (da) | 1970-02-23 |
| DE1568950A1 (de) | 1970-11-26 |
| DE1793662A1 (de) | 1972-08-03 |
| NL6605375A (xx) | 1966-10-24 |
| SE323674B (xx) | 1970-05-11 |
| FI44906B (xx) | 1971-11-01 |
| DE1568951A1 (de) | 1970-06-18 |
| NL128816C (xx) | |
| CH471833A (fr) | 1969-04-30 |
| ES325755A1 (es) | 1967-02-16 |
| NL6605174A (xx) | 1966-10-24 |
| BR6679615D0 (pt) | 1973-10-23 |
| US3413286A (en) | 1968-11-26 |
| BE679820A (xx) | 1966-10-03 |
| FR5645M (xx) | 1967-12-26 |
| NO127346B (xx) | 1973-06-12 |
| DE1793662B2 (de) | 1973-04-19 |
| BR6678805D0 (pt) | 1973-09-18 |
| BE679821A (xx) | 1966-10-03 |
| FI44905B (xx) | 1971-11-01 |
| FI44905C (fi) | 1972-02-10 |
| US3436389A (en) | 1969-04-01 |
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