CA1142925A - Substituted 4-amino-2,6-diaryl-tetrahydro-thiopyrans, the acid addition salts, process for production, use and pharmaceutical composition thereof - Google Patents
Substituted 4-amino-2,6-diaryl-tetrahydro-thiopyrans, the acid addition salts, process for production, use and pharmaceutical composition thereofInfo
- Publication number
- CA1142925A CA1142925A CA000367088A CA367088A CA1142925A CA 1142925 A CA1142925 A CA 1142925A CA 000367088 A CA000367088 A CA 000367088A CA 367088 A CA367088 A CA 367088A CA 1142925 A CA1142925 A CA 1142925A
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydrothiopyran
- phenyl
- formula
- diaryl
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims abstract description 24
- 150000003839 salts Chemical class 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims 6
- 239000008194 pharmaceutical composition Substances 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- -1 piperazino ring Chemical group 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- IRYSOHKKWIRVLX-UHFFFAOYSA-N dimethylamino formate Chemical compound CN(C)OC=O IRYSOHKKWIRVLX-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 229960002748 norepinephrine Drugs 0.000 claims description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- QKZUDBGFYSVFJF-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-phenylthian-4-one Chemical compound C1=CC(Cl)=CC=C1C1SC(C=2C=CC=CC=2)CC(=O)C1 QKZUDBGFYSVFJF-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- ICRGSDQNZOTTTN-UHFFFAOYSA-N 2,6-bis(4-methoxyphenyl)thian-4-one Chemical compound C1=CC(OC)=CC=C1C1SC(C=2C=CC(OC)=CC=2)CC(=O)C1 ICRGSDQNZOTTTN-UHFFFAOYSA-N 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 1
- DVYSFZJKLYKOIF-UHFFFAOYSA-N methylamino formate Chemical compound CNOC=O DVYSFZJKLYKOIF-UHFFFAOYSA-N 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
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- 238000007792 addition Methods 0.000 description 19
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- 239000004480 active ingredient Substances 0.000 description 7
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- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
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- 229910052623 talc Inorganic materials 0.000 description 3
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XWSBAVVPGULZOY-UHFFFAOYSA-N n-(thian-4-ylidene)hydroxylamine Chemical class ON=C1CCSCC1 XWSBAVVPGULZOY-UHFFFAOYSA-N 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000966 norepinephrine reuptake Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229940075065 polyvinyl acetate Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- 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
- A61P25/24—Antidepressants
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (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)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2951634.5 | 1979-12-21 | ||
| DE19792951634 DE2951634A1 (de) | 1979-12-21 | 1979-12-21 | Neue substituierte 4-amino-2,6-diaryl-tetrahydrothiopyrane, deren saeureadditionssalze, verfahren zu ihrer herstellung, ihre verwendung und pharmazeutische zusammensetzungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1142925A true CA1142925A (en) | 1983-03-15 |
Family
ID=6089212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000367088A Expired CA1142925A (en) | 1979-12-21 | 1980-12-18 | Substituted 4-amino-2,6-diaryl-tetrahydro-thiopyrans, the acid addition salts, process for production, use and pharmaceutical composition thereof |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4297354A (en, 2012) |
| EP (1) | EP0031456B1 (en, 2012) |
| JP (1) | JPS5699473A (en, 2012) |
| AT (1) | ATE7141T1 (en, 2012) |
| AU (1) | AU537086B2 (en, 2012) |
| CA (1) | CA1142925A (en, 2012) |
| DE (2) | DE2951634A1 (en, 2012) |
| DK (1) | DK537180A (en, 2012) |
| ES (1) | ES497949A0 (en, 2012) |
| FI (1) | FI66608C (en, 2012) |
| GR (1) | GR72839B (en, 2012) |
| IL (1) | IL61771A (en, 2012) |
| NO (1) | NO151934C (en, 2012) |
| NZ (1) | NZ195889A (en, 2012) |
| PH (1) | PH15866A (en, 2012) |
| PT (1) | PT72255B (en, 2012) |
| ZA (1) | ZA807952B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0310551B1 (de) * | 1987-09-30 | 1994-01-26 | Ciba-Geigy Ag | Phenolische Thianderivate |
| WO2011033115A2 (en) | 2009-09-18 | 2011-03-24 | Centre National De La Recherche Scientifique | Compounds useful against kinetoplastideae parasites |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419555A (en) * | 1965-10-24 | 1968-12-31 | Robins Co Inc A H | 2-aryl-tetrahydropyran-3-amines |
| US3787442A (en) * | 1973-01-26 | 1974-01-22 | American Home Prod | Tetrahydro-2h-thiopyran-4-sulfamic acids and salts |
-
1979
- 1979-12-21 DE DE19792951634 patent/DE2951634A1/de not_active Withdrawn
-
1980
- 1980-11-22 EP EP80107291A patent/EP0031456B1/de not_active Expired
- 1980-11-22 DE DE8080107291T patent/DE3067580D1/de not_active Expired
- 1980-11-22 AT AT80107291T patent/ATE7141T1/de not_active IP Right Cessation
- 1980-12-05 GR GR63558A patent/GR72839B/el unknown
- 1980-12-15 US US06/216,423 patent/US4297354A/en not_active Expired - Fee Related
- 1980-12-17 DK DK537180A patent/DK537180A/da not_active Application Discontinuation
- 1980-12-18 NO NO803863A patent/NO151934C/no unknown
- 1980-12-18 CA CA000367088A patent/CA1142925A/en not_active Expired
- 1980-12-19 PT PT72255A patent/PT72255B/pt unknown
- 1980-12-19 NZ NZ195889A patent/NZ195889A/xx unknown
- 1980-12-19 FI FI803970A patent/FI66608C/fi not_active IP Right Cessation
- 1980-12-19 AU AU65601/80A patent/AU537086B2/en not_active Ceased
- 1980-12-19 JP JP18031280A patent/JPS5699473A/ja active Pending
- 1980-12-19 IL IL61771A patent/IL61771A/xx unknown
- 1980-12-19 ES ES497949A patent/ES497949A0/es active Granted
- 1980-12-19 ZA ZA00807952A patent/ZA807952B/xx unknown
- 1980-12-21 PH PH25044A patent/PH15866A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ195889A (en) | 1983-09-02 |
| ATE7141T1 (de) | 1984-05-15 |
| NO803863L (no) | 1981-06-22 |
| NO151934B (no) | 1985-03-25 |
| IL61771A0 (en) | 1981-01-30 |
| AU6560180A (en) | 1981-06-25 |
| PH15866A (en) | 1983-04-13 |
| FI66608C (fi) | 1984-11-12 |
| GR72839B (en, 2012) | 1983-12-07 |
| PT72255B (de) | 1982-07-13 |
| FI803970L (fi) | 1981-06-22 |
| ES8202552A1 (es) | 1982-02-01 |
| EP0031456B1 (de) | 1984-04-18 |
| JPS5699473A (en) | 1981-08-10 |
| ES497949A0 (es) | 1982-02-01 |
| DK537180A (da) | 1981-06-22 |
| DE3067580D1 (en) | 1984-05-24 |
| US4297354A (en) | 1981-10-27 |
| FI66608B (fi) | 1984-07-31 |
| ZA807952B (en) | 1982-08-25 |
| EP0031456A1 (de) | 1981-07-08 |
| NO151934C (no) | 1985-07-03 |
| AU537086B2 (en) | 1984-06-07 |
| DE2951634A1 (de) | 1981-07-16 |
| PT72255A (de) | 1981-01-01 |
| IL61771A (en) | 1984-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |