NO135366B - - Google Patents
Download PDFInfo
- Publication number
- NO135366B NO135366B NO398/71A NO39871A NO135366B NO 135366 B NO135366 B NO 135366B NO 398/71 A NO398/71 A NO 398/71A NO 39871 A NO39871 A NO 39871A NO 135366 B NO135366 B NO 135366B
- Authority
- NO
- Norway
- Prior art keywords
- denotes
- group
- compound
- optionally
- general formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 230000000694 effects Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 claims description 5
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 claims description 5
- QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 230000002048 spasmolytic effect Effects 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- BKBBHXQBVJMMHW-UHFFFAOYSA-N 6,7-dihydro-5h-dibenzo[2,1-b:2',1'-e][7]annulene Chemical class C1CCC2=CC=CC=C2C2=CC=CC=C21 BKBBHXQBVJMMHW-UHFFFAOYSA-N 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000000739 antihistaminic agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 150000001414 amino alcohols Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- -1 carbon hydrogen Chemical class 0.000 description 4
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229960000520 diphenhydramine Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000001004 anti-acetylcholinic effect Effects 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JSUAJTLKVREZHV-UHFFFAOYSA-N 1-[4-(1-pyrrolidinyl)but-2-ynyl]pyrrolidine Chemical compound C1CCCN1CC#CCN1CCCC1 JSUAJTLKVREZHV-UHFFFAOYSA-N 0.000 description 1
- WZNUGVQVDDBILL-UHFFFAOYSA-N 1-chlorocyclohepta-1,3-diene Chemical compound ClC1=CC=CCCC1 WZNUGVQVDDBILL-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NKRLLPCWCPIQPL-UHFFFAOYSA-N 2-pyrrolidin-3-ylethanol Chemical compound OCCC1CCNC1 NKRLLPCWCPIQPL-UHFFFAOYSA-N 0.000 description 1
- GRTFPMFJLQWJEI-UHFFFAOYSA-N 4-(diethylamino)-2-methylbutan-1-ol Chemical compound CCN(CC)CCC(C)CO GRTFPMFJLQWJEI-UHFFFAOYSA-N 0.000 description 1
- BIZAEBQHHZWQIT-UHFFFAOYSA-N 6,7-dihydro-5h-dibenzo[2,1-b:2',1'-e][7]annulen-5-ol Chemical class OC1CCC2=CC=CC=C2C2=CC=CC=C12 BIZAEBQHHZWQIT-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 244000309464 bull Species 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 150000007654 dibenzocycloheptanes Chemical class 0.000 description 1
- 230000000105 effect on tremor Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 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
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702005002 DE2005002A1 (da) | 1970-02-04 | 1970-02-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135366B true NO135366B (da) | 1976-12-20 |
| NO135366C NO135366C (no) | 1977-03-30 |
Family
ID=5761386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO398/71A NO135366C (no) | 1970-02-04 | 1971-02-03 | Analogifremgangsm}te for fremstilling av terapeutisk aktive estere av fluocinolon-acetonid. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3740392A (da) |
| JP (1) | JPS5224016B1 (da) |
| AT (1) | AT301773B (da) |
| BE (1) | BE762487A (da) |
| BG (1) | BG17565A3 (da) |
| CA (1) | CA918635A (da) |
| CH (1) | CH571541A5 (da) |
| CS (1) | CS161769B2 (da) |
| DE (1) | DE2005002A1 (da) |
| DK (1) | DK126424B (da) |
| ES (1) | ES387494A1 (da) |
| FI (1) | FI48584C (da) |
| FR (1) | FR2081489B1 (da) |
| GB (1) | GB1318817A (da) |
| IE (1) | IE34930B1 (da) |
| IL (1) | IL36127A (da) |
| NL (1) | NL7101407A (da) |
| NO (1) | NO135366C (da) |
| PL (1) | PL81653B1 (da) |
| RO (1) | RO56931A (da) |
| SE (1) | SE369715B (da) |
| SU (1) | SU382281A3 (da) |
| YU (1) | YU18371A (da) |
| ZA (1) | ZA71661B (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3867528A (en) * | 1973-10-11 | 1975-02-18 | American Cyanamid Co | Steroidal topical cream base |
| US3892856A (en) * | 1974-04-10 | 1975-07-01 | Squibb & Sons Inc | Topical steroid formulation |
| US3970646A (en) * | 1974-04-24 | 1976-07-20 | Ortho Pharmaceutical Corporation | Halo-steroidal thioketals |
| US4221786A (en) * | 1978-06-20 | 1980-09-09 | Ciba-Geigy Corporation | Novel halogenopregnadienes and process for the manufacture thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053836A (en) * | 1961-07-14 | 1962-09-11 | Olin Mathieson | Acetals and ketals of 16alpha, 17alpha-dihydroxyprogesterones |
| DE1252678B (de) * | 1965-06-05 | 1967-10-26 | Dr, Karl Thomae GmbH, Biber ach/Riß | Verfahren zur Herstellung neuer Corticosteroid 21ester |
| US3374230A (en) * | 1966-04-26 | 1968-03-19 | Schering Corp | Acetylation of steroidal alcohols with ketene |
-
1970
- 1970-02-04 DE DE19702005002 patent/DE2005002A1/de not_active Withdrawn
-
1971
- 1971-01-20 FI FI710145A patent/FI48584C/fi active
- 1971-01-21 ES ES387494A patent/ES387494A1/es not_active Expired
- 1971-01-22 RO RO65682A patent/RO56931A/ro unknown
- 1971-01-25 CS CS530A patent/CS161769B2/cs unknown
- 1971-01-26 US US00109975A patent/US3740392A/en not_active Expired - Lifetime
- 1971-01-28 SU SU1617460A patent/SU382281A3/ru active
- 1971-01-28 YU YU00183/71A patent/YU18371A/xx unknown
- 1971-02-01 BG BG16699A patent/BG17565A3/xx unknown
- 1971-02-03 AT AT90971A patent/AT301773B/de not_active IP Right Cessation
- 1971-02-03 DK DK47271AA patent/DK126424B/da unknown
- 1971-02-03 PL PL1971145989A patent/PL81653B1/pl unknown
- 1971-02-03 NL NL7101407A patent/NL7101407A/xx not_active Application Discontinuation
- 1971-02-03 ZA ZA710661A patent/ZA71661B/xx unknown
- 1971-02-03 IL IL36127A patent/IL36127A/xx unknown
- 1971-02-03 CH CH157271A patent/CH571541A5/xx not_active IP Right Cessation
- 1971-02-03 JP JP46004201A patent/JPS5224016B1/ja active Pending
- 1971-02-03 BE BE762487A patent/BE762487A/xx unknown
- 1971-02-03 NO NO398/71A patent/NO135366C/no unknown
- 1971-02-04 CA CA104443A patent/CA918635A/en not_active Expired
- 1971-02-04 SE SE01399/71A patent/SE369715B/xx unknown
- 1971-02-04 FR FR7103754A patent/FR2081489B1/fr not_active Expired
- 1971-02-04 IE IE131/71A patent/IE34930B1/xx unknown
- 1971-04-19 GB GB2113271A patent/GB1318817A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI48584C (fi) | 1974-11-11 |
| NO135366C (no) | 1977-03-30 |
| JPS5224016B1 (da) | 1977-06-28 |
| IL36127A0 (en) | 1971-04-28 |
| FI48584B (da) | 1974-07-31 |
| CA918635A (en) | 1973-01-09 |
| GB1318817A (en) | 1973-05-31 |
| NL7101407A (da) | 1971-08-06 |
| BG17565A3 (da) | 1973-11-10 |
| CH571541A5 (da) | 1976-01-15 |
| IE34930B1 (en) | 1975-10-01 |
| DE2005002A1 (da) | 1971-08-12 |
| IE34930L (en) | 1971-08-04 |
| SE369715B (da) | 1974-09-16 |
| RO56931A (da) | 1975-02-15 |
| US3740392A (en) | 1973-06-19 |
| ZA71661B (en) | 1971-11-24 |
| DK126424B (da) | 1973-07-16 |
| BE762487A (fr) | 1971-08-03 |
| YU18371A (en) | 1978-10-31 |
| IL36127A (en) | 1974-06-30 |
| FR2081489B1 (da) | 1974-11-15 |
| PL81653B1 (da) | 1975-08-30 |
| ES387494A1 (es) | 1973-05-01 |
| CS161769B2 (da) | 1975-06-10 |
| FR2081489A1 (da) | 1971-12-03 |
| AT301773B (de) | 1972-09-25 |
| SU382281A3 (da) | 1973-05-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Turner et al. | Studies on imidazole compounds. I. 4-Methylimidazole and related compounds | |
| DK153397B (da) | Analogifremgangsmaade til fremstilling af 1,3,4-trisubstituerede 4-arylpiperidiner eller farmaceutisk acceptable syreadditionssalte deraf | |
| JPH08502275A (ja) | ５−ｈｔ▲下４▼レセプターアンタゴニスト用複素環式縮合安息香酸誘導体 | |
| DK173674B1 (da) | Anti-allergiske præparater indeholdende N-heterocyclyl-4-piperidinaminer, N-heterocyclyl-4-piperidinaminer til brug som antiallergikum og hidtil ukendte N-heterocyclyl-4-piperidinaminer samt fremgangsmåde til fremstilling deraf | |
| DK158980B (da) | Analogifremgangsmaade til fremstilling af 2,5-bis-(2,2,2-trifluorethoxy)-n-(2-piperidylmethyl)benzamid eller et farmaceutisk acceptabelt syreadditionssalt deraf | |
| JPH08502741A (ja) | ５−ｈｔ▲下４▼レセプターアンタゴニスト用のピペリジン誘導体 | |
| EP1940823A2 (fr) | Dérivés de la 1-amino-phtalazine substituee, leur préparation et leur application en thérapeutique | |
| US4980365A (en) | N-substituted-5,6-dimethoxy-1,2-benzisoxazole-3-propanamine and related compounds as analgesic and hypotensive agents | |
| US2683742A (en) | Nu, nu-disubstituted omega-arylmethoxy-omega-arylalkylamine derivatives | |
| JP2008530234A (ja) | Ｃｉｎｖ及びｉｂｓ−ｄ治療用のベンゾオキサゾールカルボキサミド | |
| US3480626A (en) | Certain azoniaspironortropine derivatives | |
| EP1847535A1 (en) | 1-(piperidin-4-yl)-1h-indole derivative | |
| US5708174A (en) | Heterocyclic-esters or -amides used as 5-HT4 receptor antagonists | |
| EP0836599A1 (en) | 1,6-disubstituted isochromans for treatment of migraine headaches | |
| CZ299199A3 (cs) | Oxazolidinony jako 5-HT2A antagonisty | |
| CA2131381A1 (en) | Nitrogen containing heterocyclic compounds useful as pharmaceuticals | |
| WO1994008965A1 (en) | N-alkylpiperidinyl-4-methyl carboxylic esters/amides of condensed ring systems as 5-ht4 receptor antagonists | |
| IE42978B1 (en) | Triaryl alkyl azabicyclo compounds | |
| MXPA06013520A (es) | Tetrahironaftilpiperazinas como antagonistas, agonistas inversos y agonistas parciales de 5-ht1b. | |
| US2976291A (en) | Ethers of z | |
| NO135366B (da) | ||
| US5008264A (en) | N-substituted-5,6-dimethoxy-1,2-benzisoxazole-3-propanamine and related compounds as analgesic and hypotensive agents | |
| US5030639A (en) | N-substituted-5,6-dimethoxy-1,2-benzisoxazole-3-propanamine and related compounds as analgesic and hypotensive agents | |
| WO1994017071A1 (en) | Tricyclic heterocyclic compounds as 5-ht4 receptor antagonists | |
| NO126914B (da) |