PL91807B1 - - Google Patents
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- Publication number
- PL91807B1 PL91807B1 PL1973174972A PL17497273A PL91807B1 PL 91807 B1 PL91807 B1 PL 91807B1 PL 1973174972 A PL1973174972 A PL 1973174972A PL 17497273 A PL17497273 A PL 17497273A PL 91807 B1 PL91807 B1 PL 91807B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- general formula
- compounds
- acid addition
- addition salts
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 description 5
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000005661 deetherification reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- -1 hydrochloric Chemical class 0.000 description 3
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000008896 Opium Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000007257 deesterification reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 229960001027 opium Drugs 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- KKWWFYAKOFXBEY-UHFFFAOYSA-N 3-(chloromethyl)thiophene Chemical compound ClCC=1C=CSC=1 KKWWFYAKOFXBEY-UHFFFAOYSA-N 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
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- AGANSXYIEFDATK-UHFFFAOYSA-N dichloromethane;sodium Chemical compound [Na].ClCCl AGANSXYIEFDATK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 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
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002691 malonic acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- HKOIXWVRNLGFOR-KOFBORESSA-N norcodeine Chemical compound O[C@H]([C@@H]1O2)C=C[C@H]3[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4 HKOIXWVRNLGFOR-KOFBORESSA-N 0.000 description 1
- 229950004392 norcodeine Drugs 0.000 description 1
- HKOIXWVRNLGFOR-UHFFFAOYSA-N norcodeine Natural products O1C2C(O)C=CC3C4CC5=CC=C(OC)C1=C5C23CCN4 HKOIXWVRNLGFOR-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet 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
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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Networks Using Active Elements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2245141A DE2245141A1 (de) | 1972-09-14 | 1972-09-14 | Neue n-(heteroarylmethyl)-desoxynormorphine und -norcodeine, deren saeureadditionssalze, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL91807B1 true PL91807B1 (en, 2012) | 1977-03-31 |
Family
ID=5856355
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973174974A PL91809B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174969A PL91837B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174970A PL91836B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174971A PL91829B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174972A PL91807B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973165187A PL87721B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174973A PL91808B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174968A PL90720B1 (en, 2012) | 1972-09-14 | 1973-09-13 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973174974A PL91809B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174969A PL91837B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174970A PL91836B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174971A PL91829B1 (en, 2012) | 1972-09-14 | 1973-09-13 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973165187A PL87721B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174973A PL91808B1 (en, 2012) | 1972-09-14 | 1973-09-13 | |
| PL1973174968A PL90720B1 (en, 2012) | 1972-09-14 | 1973-09-13 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3928359A (en, 2012) |
| JP (1) | JPS4966700A (en, 2012) |
| AT (1) | AT326281B (en, 2012) |
| BE (1) | BE804836A (en, 2012) |
| BG (8) | BG21229A3 (en, 2012) |
| CH (7) | CH589089A5 (en, 2012) |
| CS (8) | CS168673B2 (en, 2012) |
| DD (1) | DD109384A5 (en, 2012) |
| DE (1) | DE2245141A1 (en, 2012) |
| ES (8) | ES418563A1 (en, 2012) |
| FI (1) | FI55512C (en, 2012) |
| FR (1) | FR2199982B1 (en, 2012) |
| GB (1) | GB1449222A (en, 2012) |
| HU (1) | HU166367B (en, 2012) |
| IE (1) | IE38320B1 (en, 2012) |
| IL (1) | IL43216A (en, 2012) |
| NL (1) | NL7312621A (en, 2012) |
| NO (1) | NO139482C (en, 2012) |
| PL (8) | PL91809B1 (en, 2012) |
| RO (2) | RO70193A (en, 2012) |
| SE (1) | SE413510B (en, 2012) |
| SU (8) | SU498911A3 (en, 2012) |
| YU (2) | YU243973A (en, 2012) |
| ZA (1) | ZA737289B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4236008A (en) * | 1978-09-19 | 1980-11-25 | E. I. Du Pont De Nemours And Company | Fluorination of precursors for fluorine analogs of hydrocodone and oxycodone |
| US4241065A (en) * | 1979-07-02 | 1980-12-23 | E. I. Du Pont De Nemours And Company | Fluoro analogs of hydrocodone and oxycodone useful as analgesics, narcotic antagonists or both |
| CA2319627A1 (en) * | 1998-01-29 | 1999-08-05 | Polychip Pharmaceuticals Pty. Ltd. | Therapeutic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2107989A1 (de) * | 1971-02-19 | 1972-09-07 | Boehringer Sohn Ingelheim | N-(Furyl-methy])-morphinane, deren Säureadditionssalze sowie Verfahren zu deren Herstellung |
-
1972
- 1972-09-14 DE DE2245141A patent/DE2245141A1/de active Pending
-
1973
- 1973-09-03 AT AT761673A patent/AT326281B/de not_active IP Right Cessation
- 1973-09-07 ES ES418563A patent/ES418563A1/es not_active Expired
- 1973-09-11 CH CH198177A patent/CH589089A5/xx not_active IP Right Cessation
- 1973-09-11 US US396171A patent/US3928359A/en not_active Expired - Lifetime
- 1973-09-11 CH CH207077A patent/CH591490A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH207377A patent/CH591491A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH198077A patent/CH589088A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH207277A patent/CH605958A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH207177A patent/CH589090A5/xx not_active IP Right Cessation
- 1973-09-11 CH CH1298673A patent/CH590287A5/xx not_active IP Right Cessation
- 1973-09-12 BG BG025618A patent/BG21229A3/xx unknown
- 1973-09-12 BG BG025619A patent/BG21230A3/xx unknown
- 1973-09-12 CS CS6322A patent/CS168673B2/cs unknown
- 1973-09-12 DD DD173479A patent/DD109384A5/xx unknown
- 1973-09-12 CS CS283*[A patent/CS168675B2/cs unknown
- 1973-09-12 SU SU1962620A patent/SU498911A3/ru active
- 1973-09-12 CS CS282*[A patent/CS168674B2/cs unknown
- 1973-09-12 IE IE1630/73A patent/IE38320B1/xx unknown
- 1973-09-12 CS CS285*[A patent/CS168677B2/cs unknown
- 1973-09-12 CS CS284*[A patent/CS168676B2/cs unknown
- 1973-09-12 BG BG025616A patent/BG21227A3/xx unknown
- 1973-09-12 BG BG24524A patent/BG21412A3/xx unknown
- 1973-09-12 BG BG025614A patent/BG21225A3/xx unknown
- 1973-09-12 CS CS287*[A patent/CS168679B2/cs unknown
- 1973-09-12 CS CS288*[A patent/CS168680B2/cs unknown
- 1973-09-12 BG BG25617A patent/BG21228A3/xx unknown
- 1973-09-12 BG BG025613A patent/BG21224A3/xx unknown
- 1973-09-12 CS CS286*[A patent/CS168678B2/cs unknown
- 1973-09-12 HU HUBO1463A patent/HU166367B/hu unknown
- 1973-09-13 RO RO7382817A patent/RO70193A/ro unknown
- 1973-09-13 PL PL1973174974A patent/PL91809B1/pl unknown
- 1973-09-13 PL PL1973174969A patent/PL91837B1/pl unknown
- 1973-09-13 PL PL1973174970A patent/PL91836B1/pl unknown
- 1973-09-13 NO NO3588/73A patent/NO139482C/no unknown
- 1973-09-13 PL PL1973174971A patent/PL91829B1/pl unknown
- 1973-09-13 NL NL7312621A patent/NL7312621A/xx not_active Application Discontinuation
- 1973-09-13 JP JP48103716A patent/JPS4966700A/ja active Pending
- 1973-09-13 FI FI2853/73A patent/FI55512C/fi active
- 1973-09-13 IL IL43216A patent/IL43216A/en unknown
- 1973-09-13 PL PL1973174972A patent/PL91807B1/pl unknown
- 1973-09-13 BE BE135636A patent/BE804836A/xx unknown
- 1973-09-13 PL PL1973165187A patent/PL87721B1/pl unknown
- 1973-09-13 ZA ZA00737289A patent/ZA737289B/xx unknown
- 1973-09-13 PL PL1973174973A patent/PL91808B1/pl unknown
- 1973-09-13 YU YU02439/73A patent/YU243973A/xx unknown
- 1973-09-13 PL PL1973174968A patent/PL90720B1/pl unknown
- 1973-09-13 GB GB4314673A patent/GB1449222A/en not_active Expired
- 1973-09-13 RO RO7300076068A patent/RO63003A/ro unknown
- 1973-09-14 SE SE7312583A patent/SE413510B/xx unknown
- 1973-09-14 FR FR7333092A patent/FR2199982B1/fr not_active Expired
-
1974
- 1974-01-28 BG BG025615A patent/BG21226A3/bg unknown
- 1974-09-19 ES ES430199A patent/ES430199A1/es not_active Expired
- 1974-09-19 ES ES430201A patent/ES430201A1/es not_active Expired
- 1974-09-19 ES ES430200A patent/ES430200A1/es not_active Expired
- 1974-09-19 ES ES430203A patent/ES430203A1/es not_active Expired
- 1974-09-19 ES ES430202A patent/ES430202A1/es not_active Expired
- 1974-09-19 ES ES430198A patent/ES430198A1/es not_active Expired
- 1974-09-19 ES ES430197A patent/ES430197A1/es not_active Expired
- 1974-09-30 SU SU2063986A patent/SU505366A3/ru active
- 1974-09-30 SU SU2063380A patent/SU503524A3/ru active
- 1974-09-30 SU SU2063983A patent/SU509239A3/ru active
- 1974-09-30 SU SU2063987A patent/SU506299A3/ru active
- 1974-09-30 SU SU2063985A patent/SU503523A3/ru active
- 1974-09-30 SU SU2063984A patent/SU520049A3/ru active
- 1974-09-30 SU SU2063982A patent/SU528878A3/ru active
-
1979
- 1979-10-19 YU YU02548/79A patent/YU254879A/xx unknown
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