NO874765L - Anticholinforbindelser, farmastiske blandinger og behand lingsmetode. - Google Patents
Anticholinforbindelser, farmastiske blandinger og behand lingsmetode.Info
- Publication number
- NO874765L NO874765L NO874765A NO874765A NO874765L NO 874765 L NO874765 L NO 874765L NO 874765 A NO874765 A NO 874765A NO 874765 A NO874765 A NO 874765A NO 874765 L NO874765 L NO 874765L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- connection according
- alkyl
- methyl
- carbon atoms
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 79
- 238000000034 method Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 title description 29
- 230000001078 anti-cholinergic effect Effects 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 230000002911 mydriatic effect Effects 0.000 claims abstract description 15
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 15
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 230000032050 esterification Effects 0.000 claims abstract description 8
- 238000005886 esterification reaction Methods 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 239000002207 metabolite Substances 0.000 claims abstract description 6
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 241001465754 Metazoa Species 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 150000008051 alkyl sulfates Chemical group 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 19
- -1 bicyclic amine Chemical group 0.000 abstract description 11
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical class O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 abstract description 7
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 43
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 36
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- XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 21
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
- QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 description 21
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
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- 125000002619 bicyclic group Chemical group 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 11
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- 238000006243 chemical reaction Methods 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
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- 239000007787 solid Substances 0.000 description 8
- 208000006550 Mydriasis Diseases 0.000 description 7
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 7
- 229960004484 carbachol Drugs 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- INQWZSLKTMTMSK-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-phenylpropanoic acid Chemical compound CCOC(=O)C(C(O)=O)C1=CC=CC=C1 INQWZSLKTMTMSK-UHFFFAOYSA-N 0.000 description 5
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 5
- 229930003347 Atropine Natural products 0.000 description 5
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 5
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 229960000396 atropine Drugs 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
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- 239000000706 filtrate Substances 0.000 description 5
- 230000003301 hydrolyzing effect Effects 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 5
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- 238000007790 scraping Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- YOCUIEZMVOBCJQ-UHFFFAOYSA-N 2-methyl-2-phenylpropanedioyl dichloride Chemical compound ClC(=O)C(C)(C(Cl)=O)C1=CC=CC=C1 YOCUIEZMVOBCJQ-UHFFFAOYSA-N 0.000 description 4
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- 150000001298 alcohols Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
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- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- HRQDCDQDOPSGBR-UHFFFAOYSA-M sodium;octane-1-sulfonate Chemical compound [Na+].CCCCCCCCS([O-])(=O)=O HRQDCDQDOPSGBR-UHFFFAOYSA-M 0.000 description 3
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- ZWSVRRQIPCGRPY-UHFFFAOYSA-N 2-cyclohexyl-2-phenylpropanedioyl dichloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)(C(Cl)=O)C1CCCCC1 ZWSVRRQIPCGRPY-UHFFFAOYSA-N 0.000 description 2
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- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229940087766 mydriacyl Drugs 0.000 description 1
- WUOSYUHCXLQPQJ-UHFFFAOYSA-N n-(3-chlorophenyl)-n-methylacetamide Chemical compound CC(=O)N(C)C1=CC=CC(Cl)=C1 WUOSYUHCXLQPQJ-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- ZABUMNSTZYZRFX-UHFFFAOYSA-N octan-3-yl 2-phenylacetate Chemical compound CCC(CCCCC)OC(CC1=CC=CC=C1)=O ZABUMNSTZYZRFX-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000010344 pupil dilation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83994186A | 1986-03-17 | 1986-03-17 | |
| PCT/US1987/000533 WO1987005603A1 (en) | 1986-03-17 | 1987-03-17 | Anticholinergic compounds, pharmaceutical compositions and method of treatment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO874765D0 NO874765D0 (no) | 1987-11-16 |
| NO874765L true NO874765L (no) | 1988-01-14 |
Family
ID=25281041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO874765A NO874765L (no) | 1986-03-17 | 1987-11-16 | Anticholinforbindelser, farmastiske blandinger og behand lingsmetode. |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0238982B1 (da) |
| JP (1) | JP2672311B2 (da) |
| KR (1) | KR900007218B1 (da) |
| AT (1) | ATE86622T1 (da) |
| CA (1) | CA1328106C (da) |
| DE (1) | DE3784531T2 (da) |
| DK (1) | DK170560B1 (da) |
| ES (1) | ES2044851T3 (da) |
| FI (1) | FI87213C (da) |
| IE (1) | IE60645B1 (da) |
| NO (1) | NO874765L (da) |
| NZ (1) | NZ219653A (da) |
| WO (1) | WO1987005603A1 (da) |
| ZA (1) | ZA871948B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20050489A1 (es) * | 2003-11-04 | 2005-09-02 | Glaxo Group Ltd | Antagonistas de receptores de acetilcolina muscarinicos |
| US20080027094A1 (en) * | 2004-08-30 | 2008-01-31 | Ono Pharmaceutical Co., Ltd. | Tropane Compounds and Pharmaceutical Compositions Comprising the Same as an Active Ingredient |
| CN113321648B (zh) * | 2021-05-21 | 2022-02-11 | 常州康普药业有限公司 | 一种硫酸阿托品的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2814623A (en) * | 1955-12-05 | 1957-11-26 | Upjohn Co | Certain esters of n-methyl scopolamine quaternary ammonium salts |
| DE1670048C3 (de) * | 1966-01-26 | 1980-09-04 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue Norscopolaminderivate |
| NL7002588A (da) * | 1969-03-04 | 1970-09-08 | ||
| US3998815A (en) * | 1974-06-24 | 1976-12-21 | Interx Research Corporation | 1-hydrocarbonoyloxymethyl-3-carbamoyl or 3-carboethoxy-pyridinium salts |
-
1987
- 1987-03-16 CA CA000532123A patent/CA1328106C/en not_active Expired - Fee Related
- 1987-03-16 IE IE69887A patent/IE60645B1/en not_active IP Right Cessation
- 1987-03-17 NZ NZ219653A patent/NZ219653A/xx unknown
- 1987-03-17 EP EP87103868A patent/EP0238982B1/en not_active Expired - Lifetime
- 1987-03-17 ES ES87103868T patent/ES2044851T3/es not_active Expired - Lifetime
- 1987-03-17 JP JP62502072A patent/JP2672311B2/ja not_active Expired - Lifetime
- 1987-03-17 DE DE8787103868T patent/DE3784531T2/de not_active Expired - Lifetime
- 1987-03-17 WO PCT/US1987/000533 patent/WO1987005603A1/en active IP Right Grant
- 1987-03-17 ZA ZA871948A patent/ZA871948B/xx unknown
- 1987-03-17 AT AT87103868T patent/ATE86622T1/de not_active IP Right Cessation
- 1987-03-17 KR KR1019870701055A patent/KR900007218B1/ko not_active IP Right Cessation
- 1987-10-30 DK DK567887A patent/DK170560B1/da not_active IP Right Cessation
- 1987-11-09 FI FI874937A patent/FI87213C/fi not_active IP Right Cessation
- 1987-11-16 NO NO874765A patent/NO874765L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7203187A (en) | 1987-10-09 |
| AU595307B2 (en) | 1990-03-29 |
| CA1328106C (en) | 1994-03-29 |
| JP2672311B2 (ja) | 1997-11-05 |
| DK567887A (da) | 1987-10-30 |
| ATE86622T1 (de) | 1993-03-15 |
| DE3784531T2 (de) | 1993-06-24 |
| FI87213C (fi) | 1992-12-10 |
| NZ219653A (en) | 1990-02-26 |
| ES2044851T3 (es) | 1994-01-16 |
| ZA871948B (en) | 1987-09-07 |
| WO1987005603A1 (en) | 1987-09-24 |
| DK170560B1 (da) | 1995-10-23 |
| IE870698L (en) | 1987-09-17 |
| DK567887D0 (da) | 1987-10-30 |
| FI874937A (fi) | 1987-11-09 |
| KR900007218B1 (ko) | 1990-10-05 |
| IE60645B1 (en) | 1994-08-10 |
| EP0238982A1 (en) | 1987-09-30 |
| NO874765D0 (no) | 1987-11-16 |
| FI87213B (fi) | 1992-08-31 |
| EP0238982B1 (en) | 1993-03-10 |
| KR880701230A (ko) | 1988-07-26 |
| JPS63502898A (ja) | 1988-10-27 |
| DE3784531D1 (de) | 1993-04-15 |
| FI874937A0 (fi) | 1987-11-09 |
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