FI60013C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 1,4-etano-7-alkyl- och 1,4-etano-7-arylperhydrokinolin-6-oner - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 1,4-etano-7-alkyl- och 1,4-etano-7-arylperhydrokinolin-6-oner Download PDFInfo
- Publication number
- FI60013C FI60013C FI763152A FI763152A FI60013C FI 60013 C FI60013 C FI 60013C FI 763152 A FI763152 A FI 763152A FI 763152 A FI763152 A FI 763152A FI 60013 C FI60013 C FI 60013C
- Authority
- FI
- Finland
- Prior art keywords
- ethano
- formula
- alkyl
- designates
- therapeutic
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000001225 therapeutic effect Effects 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- -1 isoalkyl Chemical group 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- NHPWIWAGVOXDPU-UHFFFAOYSA-N 2-methylidene-1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2CCN1C(=C)C2=O NHPWIWAGVOXDPU-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 206010000496 acne Diseases 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229930003347 Atropine Natural products 0.000 description 4
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 4
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 4
- 229960000396 atropine Drugs 0.000 description 4
- 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 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 210000003405 ileum Anatomy 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 206010044565 Tremor Diseases 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 238000010254 subcutaneous injection Methods 0.000 description 3
- 239000007929 subcutaneous injection Substances 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000916 dilatatory effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- OKANYBNORCUPKZ-UHFFFAOYSA-N ethyl 2-ethyl-3-oxobutanoate Chemical compound CCOC(=O)C(CC)C(C)=O OKANYBNORCUPKZ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 230000001151 other effect Effects 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 210000003296 saliva Anatomy 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- ZATIMOAGKJEVGN-UHFFFAOYSA-N 3-methyl-1-phenylbutan-2-one Chemical compound CC(C)C(=O)CC1=CC=CC=C1 ZATIMOAGKJEVGN-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010041235 Snoring Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001022 anti-muscarinic effect Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229960002028 atropine sulfate Drugs 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000037396 body weight Effects 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000037047 psychomotor activity Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000005586 smoking cessation Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- 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
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Ophthalmology & Optometry (AREA)
- Child & Adolescent Psychology (AREA)
- Addiction (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL4845375 | 1975-11-11 | ||
| IL48453A IL48453A (en) | 1975-11-11 | 1975-11-11 | Substituted 6-oxa-1-azatricyclo-(6.2.2.0 )dodecan-5-ones and 1,4-ethano-5-oxo octa (or decahydro)quinoline,their preparation and pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI763152A FI763152A (fr) | 1977-05-12 |
| FI60013B FI60013B (fi) | 1981-07-31 |
| FI60013C true FI60013C (fi) | 1981-11-10 |
Family
ID=11048546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI763152A FI60013C (fi) | 1975-11-11 | 1976-11-03 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 1,4-etano-7-alkyl- och 1,4-etano-7-arylperhydrokinolin-6-oner |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4083985A (fr) |
| JP (2) | JPS6045198B2 (fr) |
| AR (1) | AR213184A1 (fr) |
| AT (1) | AT355035B (fr) |
| AU (1) | AU511347B2 (fr) |
| BE (1) | BE848227A (fr) |
| CA (1) | CA1078385A (fr) |
| CH (2) | CH635102A5 (fr) |
| DE (1) | DE2650876A1 (fr) |
| DK (1) | DK507376A (fr) |
| ES (1) | ES453162A1 (fr) |
| FI (1) | FI60013C (fr) |
| FR (1) | FR2331339A1 (fr) |
| GB (1) | GB1571511A (fr) |
| IL (1) | IL48453A (fr) |
| IN (1) | IN145202B (fr) |
| MX (1) | MX4767E (fr) |
| NL (1) | NL7612427A (fr) |
| NO (1) | NO144927C (fr) |
| NZ (1) | NZ182556A (fr) |
| SE (1) | SE435929B (fr) |
| ZA (1) | ZA766663B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4183938A (en) * | 1975-11-11 | 1980-01-15 | The Purdue Frederick Company | 1,8-Ethano-5-oxo-octa- and -decahydroquinolines and mydriatic compositions thereof |
| US4855290A (en) | 1985-05-10 | 1989-08-08 | State Of Israel, Represented By Prime Minister's Office, Israel Institute For Biological Research | Derivatives of quinuclidine |
| US4876260A (en) * | 1987-10-28 | 1989-10-24 | State Of Israel, Israel Institute Of Biological Research | Oxathiolanes |
| JPH0523864Y2 (fr) * | 1989-09-05 | 1993-06-17 | ||
| US5407938A (en) * | 1990-04-10 | 1995-04-18 | Israel Institute For Biological Research | Certain 1-methyl-piperidine-4-spiro-4'-(1'-3'-oxazolines) and corresponding -(1',3' thiazolines) |
| US5852029A (en) * | 1990-04-10 | 1998-12-22 | Israel Institute For Biological Research | Aza spiro compounds acting on the cholinergic system with muscarinic agonist activity |
| JPH0518551U (ja) * | 1991-08-28 | 1993-03-09 | 亀吉 立花 | ぶら下がり健康器 |
| US5521193A (en) * | 1992-06-24 | 1996-05-28 | G. D. Searle & Co. | Benzimidazole compounds |
| US5280028A (en) * | 1992-06-24 | 1994-01-18 | G. D. Searle & Co. | Benzimidazole compounds |
| US5534521A (en) * | 1993-06-23 | 1996-07-09 | G. D. Searle & Co. | Benzimidazole compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3857837A (en) * | 1968-07-02 | 1974-12-31 | Hoffmann La Roche | Processes and intermediated for quinine, quinidine, isomers and derivatives thereof |
-
1975
- 1975-11-11 IL IL48453A patent/IL48453A/xx unknown
-
1976
- 1976-02-06 US US05/655,650 patent/US4083985A/en not_active Expired - Lifetime
- 1976-10-28 AR AR265267A patent/AR213184A1/es active
- 1976-11-03 FI FI763152A patent/FI60013C/fi not_active IP Right Cessation
- 1976-11-06 DE DE19762650876 patent/DE2650876A1/de not_active Ceased
- 1976-11-08 ZA ZA766663A patent/ZA766663B/xx unknown
- 1976-11-08 NZ NZ182556A patent/NZ182556A/xx unknown
- 1976-11-09 NL NL7612427A patent/NL7612427A/xx not_active Application Discontinuation
- 1976-11-10 CA CA265,344A patent/CA1078385A/fr not_active Expired
- 1976-11-10 CH CH1417776A patent/CH635102A5/de not_active IP Right Cessation
- 1976-11-10 GB GB46748/76A patent/GB1571511A/en not_active Expired
- 1976-11-10 ES ES453162A patent/ES453162A1/es not_active Expired
- 1976-11-10 FR FR7634034A patent/FR2331339A1/fr active Granted
- 1976-11-10 DK DK507376A patent/DK507376A/da not_active Application Discontinuation
- 1976-11-10 BE BE172272A patent/BE848227A/fr not_active IP Right Cessation
- 1976-11-10 IN IN2028/CAL/1976A patent/IN145202B/en unknown
- 1976-11-10 NO NO763820A patent/NO144927C/no unknown
- 1976-11-11 JP JP51136167A patent/JPS6045198B2/ja not_active Expired
- 1976-11-11 AU AU19552/76A patent/AU511347B2/en not_active Expired
- 1976-11-11 MX MX765119U patent/MX4767E/es unknown
- 1976-11-11 AT AT839476A patent/AT355035B/de not_active IP Right Cessation
-
1980
- 1980-05-05 SE SE8003351A patent/SE435929B/sv not_active IP Right Cessation
-
1982
- 1982-04-30 CH CH267282A patent/CH640234A5/de not_active IP Right Cessation
-
1984
- 1984-08-10 JP JP59166668A patent/JPS6043348B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1078385A (fr) | 1980-05-27 |
| AU511347B2 (en) | 1980-08-14 |
| IL48453A0 (en) | 1976-01-30 |
| MX4767E (es) | 1982-09-08 |
| JPS5283396A (en) | 1977-07-12 |
| CH640234A5 (de) | 1983-12-30 |
| FI763152A (fr) | 1977-05-12 |
| FR2331339B1 (fr) | 1980-04-04 |
| JPS6043348B2 (ja) | 1985-09-27 |
| SE8003351L (sv) | 1980-05-05 |
| NZ182556A (en) | 1979-10-25 |
| NL7612427A (nl) | 1977-05-13 |
| NO144927B (no) | 1981-08-31 |
| ATA839476A (de) | 1979-07-15 |
| AT355035B (de) | 1980-02-11 |
| GB1571511A (en) | 1980-07-16 |
| US4083985A (en) | 1978-04-11 |
| IN145202B (fr) | 1978-09-09 |
| CH635102A5 (de) | 1983-03-15 |
| FR2331339A1 (fr) | 1977-06-10 |
| NO763820L (fr) | 1977-05-12 |
| BE848227A (fr) | 1977-03-01 |
| JPS60120876A (ja) | 1985-06-28 |
| AR213184A1 (es) | 1978-12-29 |
| SE435929B (sv) | 1984-10-29 |
| NO144927C (no) | 1981-12-09 |
| DK507376A (da) | 1977-05-12 |
| DE2650876A1 (de) | 1977-05-18 |
| ZA766663B (en) | 1977-10-26 |
| JPS6045198B2 (ja) | 1985-10-08 |
| FI60013B (fi) | 1981-07-31 |
| IL48453A (en) | 1980-06-30 |
| ES453162A1 (es) | 1977-11-01 |
| AU1955276A (en) | 1978-05-18 |
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