FI60395C - Foerfarande foer framstaellning av 2-bensofuranyl-n-substituerade acetamidoximderivat med hoegt blodtryck foerhindrande verkan - Google Patents
Foerfarande foer framstaellning av 2-bensofuranyl-n-substituerade acetamidoximderivat med hoegt blodtryck foerhindrande verkan Download PDFInfo
- Publication number
- FI60395C FI60395C FI763604A FI763604A FI60395C FI 60395 C FI60395 C FI 60395C FI 763604 A FI763604 A FI 763604A FI 763604 A FI763604 A FI 763604A FI 60395 C FI60395 C FI 60395C
- Authority
- FI
- Finland
- Prior art keywords
- benzofuranyl
- ethyl
- preparation
- hypertension
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 19
- 238000010992 reflux Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical class CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- -1 2-ethyl-3-benzofuranyl Chemical group 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 230000004872 arterial blood pressure Effects 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 206010020772 Hypertension Diseases 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 241000700159 Rattus Species 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- JYXQXKHTALMLNI-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)-n-hydroxy-n'-(2-morpholin-4-ylethyl)ethanimidamide Chemical compound CCC=1OC2=CC=CC=C2C=1CC(NO)=NCCN1CCOCC1 JYXQXKHTALMLNI-UHFFFAOYSA-N 0.000 description 10
- 230000007423 decrease Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000002220 antihypertensive agent Substances 0.000 description 7
- 230000000144 pharmacologic effect Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 230000036325 urinary excretion Effects 0.000 description 7
- 230000002354 daily effect Effects 0.000 description 6
- 210000005036 nerve Anatomy 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000029142 excretion Effects 0.000 description 5
- 210000003734 kidney Anatomy 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000002889 sympathetic effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 3
- 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 3
- 229940030600 antihypertensive agent Drugs 0.000 description 3
- 208000015345 genetic hypertension Diseases 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 229910001414 potassium ion Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 231100000816 toxic dose Toxicity 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 210000004100 adrenal gland Anatomy 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 229940127088 antihypertensive drug Drugs 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229960004486 desoxycorticosterone acetate Drugs 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QAFYJWGSPQYTIH-UHFFFAOYSA-N 2-(3,5-dihydroxyanilino)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC1=CC(O)=CC(O)=C1 QAFYJWGSPQYTIH-UHFFFAOYSA-N 0.000 description 1
- YCCKYDULBTUVPT-UHFFFAOYSA-N 2-(5-chloro-2-ethyl-1-benzofuran-3-yl)-n-hydroxy-n'-(2-morpholin-4-ylethyl)ethanimidamide Chemical compound CCC=1OC2=CC=C(Cl)C=C2C=1CC(NO)=NCCN1CCOCC1 YCCKYDULBTUVPT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- ZLMHKIJMABRPGM-UHFFFAOYSA-N Cl.Cl.C(C(C)C)C=1OC2=C(C1CC(NCCN1CCOCC1)=NO)C=CC=C2 Chemical compound Cl.Cl.C(C(C)C)C=1OC2=C(C1CC(NCCN1CCOCC1)=NO)C=CC=C2 ZLMHKIJMABRPGM-UHFFFAOYSA-N 0.000 description 1
- UMNWBMAXNBROMK-UHFFFAOYSA-N Cl.Cl.C(C)(C)C=1OC2=C(C1CC(NCCN1CCOCC1)=NO)C=CC=C2 Chemical compound Cl.Cl.C(C)(C)C=1OC2=C(C1CC(NCCN1CCOCC1)=NO)C=CC=C2 UMNWBMAXNBROMK-UHFFFAOYSA-N 0.000 description 1
- VDLXLGWCASQCGK-UHFFFAOYSA-N Cl.Cl.C(C)C=1OC2=C(C1CC(NCCN(CCC)CCC)=NO)C=CC=C2 Chemical compound Cl.Cl.C(C)C=1OC2=C(C1CC(NCCN(CCC)CCC)=NO)C=CC=C2 VDLXLGWCASQCGK-UHFFFAOYSA-N 0.000 description 1
- ALFUDVXQGUEQHX-UHFFFAOYSA-N Cl.Cl.C(CCC)C=1OC2=C(C1CC(NCCN1CCOCC1)=NO)C=CC=C2 Chemical compound Cl.Cl.C(CCC)C=1OC2=C(C1CC(NCCN1CCOCC1)=NO)C=CC=C2 ALFUDVXQGUEQHX-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 206010057615 Endocrine hypertension Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000551546 Minerva Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 241000489523 Veratrum Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical class C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 229940119740 deoxycorticosterone Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FOJBQTQQONWJDQ-UHFFFAOYSA-N n'-hydroxy-2-morpholin-4-ylethanimidamide Chemical compound O\N=C(/N)CN1CCOCC1 FOJBQTQQONWJDQ-UHFFFAOYSA-N 0.000 description 1
- 210000004237 neck muscle Anatomy 0.000 description 1
- 230000001272 neurogenic effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 229940057613 veratrum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB52475/75A GB1508210A (en) | 1975-12-22 | 1975-12-22 | Benzofuran-derived amidoximes and process for preparing the same |
| GB5247575 | 1975-12-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI763604A7 FI763604A7 (en:Method) | 1977-06-23 |
| FI60395B FI60395B (fi) | 1981-09-30 |
| FI60395C true FI60395C (fi) | 1982-01-11 |
Family
ID=10464059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI763604A FI60395C (fi) | 1975-12-22 | 1976-12-15 | Foerfarande foer framstaellning av 2-bensofuranyl-n-substituerade acetamidoximderivat med hoegt blodtryck foerhindrande verkan |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS52102268A (en:Method) |
| AR (1) | AR212605A1 (en:Method) |
| AT (1) | AT354430B (en:Method) |
| AU (1) | AU503931B2 (en:Method) |
| BE (1) | BE849430A (en:Method) |
| CA (1) | CA1080723A (en:Method) |
| CH (1) | CH617688A5 (en:Method) |
| DD (1) | DD127762A5 (en:Method) |
| DE (1) | DE2657902A1 (en:Method) |
| DK (1) | DK577276A (en:Method) |
| ES (1) | ES454421A1 (en:Method) |
| FI (1) | FI60395C (en:Method) |
| FR (1) | FR2336127A1 (en:Method) |
| GB (1) | GB1508210A (en:Method) |
| HU (1) | HU176557B (en:Method) |
| IE (1) | IE44753B1 (en:Method) |
| IT (1) | IT1123948B (en:Method) |
| MX (1) | MX3927E (en:Method) |
| NL (1) | NL7613753A (en:Method) |
| NO (1) | NO144794C (en:Method) |
| NZ (1) | NZ182809A (en:Method) |
| OA (1) | OA05521A (en:Method) |
| PL (1) | PL102695B1 (en:Method) |
| PT (1) | PT65971B (en:Method) |
| SE (1) | SE429233B (en:Method) |
| SU (1) | SU598564A3 (en:Method) |
| YU (1) | YU309376A (en:Method) |
| ZA (1) | ZA767241B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3398941A1 (en) * | 2017-05-03 | 2018-11-07 | AXXAM S.p.A. | Heterocyclic p2x7 antagonists |
-
1975
- 1975-12-22 GB GB52475/75A patent/GB1508210A/en not_active Expired
-
1976
- 1976-12-03 IE IE2663/76A patent/IE44753B1/en unknown
- 1976-12-06 ZA ZA767241A patent/ZA767241B/xx unknown
- 1976-12-06 NZ NZ182809A patent/NZ182809A/xx unknown
- 1976-12-10 NL NL7613753A patent/NL7613753A/xx not_active Application Discontinuation
- 1976-12-13 AR AR265814A patent/AR212605A1/es active
- 1976-12-14 AU AU20534/76A patent/AU503931B2/en not_active Expired
- 1976-12-14 FR FR7637622A patent/FR2336127A1/fr active Granted
- 1976-12-15 BE BE173280A patent/BE849430A/xx not_active IP Right Cessation
- 1976-12-15 MX MX765235U patent/MX3927E/es unknown
- 1976-12-15 CA CA267,918A patent/CA1080723A/en not_active Expired
- 1976-12-15 FI FI763604A patent/FI60395C/fi not_active IP Right Cessation
- 1976-12-15 PT PT65971A patent/PT65971B/pt unknown
- 1976-12-20 CH CH1603476A patent/CH617688A5/fr not_active IP Right Cessation
- 1976-12-20 ES ES454421A patent/ES454421A1/es not_active Expired
- 1976-12-20 YU YU03093/76A patent/YU309376A/xx unknown
- 1976-12-21 DK DK577276A patent/DK577276A/da not_active Application Discontinuation
- 1976-12-21 AT AT948476A patent/AT354430B/de not_active IP Right Cessation
- 1976-12-21 HU HU76LA901A patent/HU176557B/hu unknown
- 1976-12-21 SU SU762430683A patent/SU598564A3/ru active
- 1976-12-21 PL PL1976194589A patent/PL102695B1/pl unknown
- 1976-12-21 NO NO76764332A patent/NO144794C/no unknown
- 1976-12-21 DE DE19762657902 patent/DE2657902A1/de not_active Withdrawn
- 1976-12-21 IT IT7630679A patent/IT1123948B/it active
- 1976-12-21 SE SE7614368A patent/SE429233B/xx unknown
- 1976-12-22 JP JP15558976A patent/JPS52102268A/ja active Pending
- 1976-12-22 DD DD7600196548A patent/DD127762A5/xx unknown
- 1976-12-22 OA OA56023A patent/OA05521A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SANOFI |