PL130647B1 - Process for preparing substituted derivatives of pyridazine - Google Patents
Process for preparing substituted derivatives of pyridazine Download PDFInfo
- Publication number
- PL130647B1 PL130647B1 PL1982237809A PL23780982A PL130647B1 PL 130647 B1 PL130647 B1 PL 130647B1 PL 1982237809 A PL1982237809 A PL 1982237809A PL 23780982 A PL23780982 A PL 23780982A PL 130647 B1 PL130647 B1 PL 130647B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- optionally
- solvent
- pyridazine
- reactions
- Prior art date
Links
- 150000004892 pyridazines Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical compound ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- -1 alkyl radical Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 230000003291 dopaminomimetic effect Effects 0.000 description 8
- LDMWSLGGVTVJPG-UHFFFAOYSA-N minaprine Chemical compound CC1=CC(C=2C=CC=CC=2)=NN=C1NCCN1CCOCC1 LDMWSLGGVTVJPG-UHFFFAOYSA-N 0.000 description 7
- 229960004758 minaprine Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 206010015995 Eyelid ptosis Diseases 0.000 description 5
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 5
- 230000001430 anti-depressive effect Effects 0.000 description 5
- 239000000935 antidepressant agent Substances 0.000 description 5
- 229940005513 antidepressants Drugs 0.000 description 5
- 230000002474 noradrenergic effect Effects 0.000 description 5
- 201000003004 ptosis Diseases 0.000 description 5
- 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 5
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 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 4
- 229960003147 reserpine Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- NFXCUPVBISCOSF-UHFFFAOYSA-N propan-2-ol;dihydrochloride Chemical compound Cl.Cl.CC(C)O NFXCUPVBISCOSF-UHFFFAOYSA-N 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- AXMMVYLSXYIGDK-UHFFFAOYSA-N 3-chloro-4-(4-methoxyphenyl)pyridazine Chemical compound C1=CC(OC)=CC=C1C1=CC=NN=C1Cl AXMMVYLSXYIGDK-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CDXUNFOKYLKPDR-UHFFFAOYSA-N Cl.O1CCN(CC1)CCNC=1N=NC=C(C1)C1=CC=CC=C1 Chemical compound Cl.O1CCN(CC1)CCNC=1N=NC=C(C1)C1=CC=CC=C1 CDXUNFOKYLKPDR-UHFFFAOYSA-N 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- KXEMQEGRZWUKJS-UHFFFAOYSA-N Raufloridine Natural products COC1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 231100000369 acute toxicity data Toxicity 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002582 psychostimulating effect Effects 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8115380A FR2510998B1 (fr) | 1981-08-07 | 1981-08-07 | Nouveaux derives amines de la pyridazine, leur procede de preparation et les medicaments, a action desinhibitrice, qui en comportent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL237809A1 PL237809A1 (en) | 1983-02-28 |
| PL130647B1 true PL130647B1 (en) | 1984-08-31 |
Family
ID=9261294
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1982237809A PL130647B1 (en) | 1981-08-07 | 1982-08-06 | Process for preparing substituted derivatives of pyridazine |
| PL1982237808A PL137199B1 (en) | 1981-08-07 | 1982-08-06 | Method of obtaining amino derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1982237808A PL137199B1 (en) | 1981-08-07 | 1982-08-06 | Method of obtaining amino derivatives |
Country Status (30)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2540113A1 (fr) * | 1983-01-27 | 1984-08-03 | Sanofi Sa | Acides derives de la pyridazine actifs sur le systeme nerveux central |
| CA1218655A (en) * | 1983-01-28 | 1987-03-03 | Kathleen Biziere | Process for the preparation of pyridazine derivatives having a psychotropic action |
| US4628088A (en) * | 1984-07-17 | 1986-12-09 | Eli Lilly And Company | Preparation of substituted pyridazines |
| DE3664772D1 (en) * | 1985-01-14 | 1989-09-07 | Boehringer Ingelheim Kg | 12-amino pyridazinoû4',5':3,4¨pyrroloû2,1-a¨isoquinolines, process for their preparation and use |
| US5461053A (en) * | 1989-02-07 | 1995-10-24 | Sanofi | Pyridazine derivatives |
| FR2642648B1 (fr) * | 1989-02-07 | 1991-06-21 | Sanofi Sa | Utilisation de derives d'alkyl-5 pyridazine comme medicaments actifs sur le systeme cholinergique |
| FR2642754B1 (fr) * | 1989-02-07 | 1991-05-24 | Sanofi Sa | Nouveaux derives de la pyridazine, procede de preparation et compositions pharmaceutiques en contenant |
| FR2654727B1 (fr) * | 1989-11-17 | 1992-03-27 | Sanofi Sa | Derives de la pyridazine, procede de preparation et compositions pharmaceutiques en contenant. |
| FR2663326B2 (fr) * | 1989-11-17 | 1992-10-16 | Sanofi Sa | Derives de la pyridazine, procede de preparation et compositions pharmaceutiques en contenant. |
| PT93060B (pt) | 1989-02-07 | 1995-12-29 | Sanofi Sa | Processo para a obtencao de derivados de piridazina e de composicoes farmaceuticas que os contem |
| US5656631A (en) * | 1989-02-07 | 1997-08-12 | Sanofi | Pyridazine derivatives |
| FR2665442B1 (fr) * | 1990-07-31 | 1992-12-04 | Sanofi Sa | Derives d'alkyl-6 pyridazine, procede de preparation et compositions pharmaceutiques en contenant. |
| FR2676444B1 (fr) * | 1991-05-16 | 1995-03-10 | Sanofi Elf | Nouveaux derives d'amino-3 pyridazines actifs sur le systeme nerveux central, procede de preparation et compositions pharmaceutiques en contenant. |
| US20100210590A1 (en) * | 1995-09-27 | 2010-08-19 | Northwestern University | Compositions and treatments for seizure-related disorders |
| US20030176437A1 (en) * | 2001-08-31 | 2003-09-18 | D.M. Watterson | Anti-inflammatory and protein kinase inhibitor compositions and related methods for downregulation of detrimental cellular responses and inhibition of cell death |
| DE60325865D1 (de) * | 2002-08-13 | 2009-03-05 | Merck Sharp & Dohme | Phenylpyridazin derivative als liganden für gaba-rezeptoren |
| BRPI0517947A (pt) | 2004-11-02 | 2008-10-21 | Univ Northwestern | composto de piridazina, composições e métodos |
| WO2006050359A2 (en) * | 2004-11-02 | 2006-05-11 | Northwestern University | Pyridazine compounds and methods |
| EP2015751A2 (en) * | 2006-04-28 | 2009-01-21 | Northwestern University | Salts of pyridazine compounds |
| EP2015750A2 (en) * | 2006-04-28 | 2009-01-21 | Northwestern University | Compositions and treatments using pyridazine compounds and cholinesterase inhibitors |
| CN101754762A (zh) * | 2006-04-28 | 2010-06-23 | 西北大学 | 用于治疗神经炎症性疾病的包含哒嗪化合物的制剂 |
| RU2555969C1 (ru) * | 2014-07-09 | 2015-07-10 | Юлия Алексеевна Щепочкина | Керамическая масса для изготовления облицовочной плитки |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1345880A (en) * | 1971-06-18 | 1974-02-06 | Cepbepe | Pyridazine derivatives |
-
1981
- 1981-08-07 FR FR8115380A patent/FR2510998B1/fr not_active Expired
-
1982
- 1982-07-21 NO NO822510A patent/NO157102C/no unknown
- 1982-07-21 NO NO822509A patent/NO157861C/no unknown
- 1982-07-23 IE IE1779/82A patent/IE53388B1/en not_active IP Right Cessation
- 1982-07-23 IE IE1778/82A patent/IE53387B1/en not_active IP Right Cessation
- 1982-07-26 GR GR68868A patent/GR76429B/el unknown
- 1982-07-26 GR GR68873A patent/GR76430B/el unknown
- 1982-07-27 IL IL66409A patent/IL66409A/xx unknown
- 1982-07-27 IL IL66408A patent/IL66408A/xx unknown
- 1982-07-29 AU AU86554/82A patent/AU548931B2/en not_active Ceased
- 1982-07-29 US US06/402,906 patent/US4508720A/en not_active Expired - Fee Related
- 1982-07-29 AU AU86553/82A patent/AU548930B2/en not_active Ceased
- 1982-07-30 PT PT75351A patent/PT75351B/pt not_active IP Right Cessation
- 1982-07-30 PT PT75350A patent/PT75350B/pt not_active IP Right Cessation
- 1982-07-30 ZA ZA825513A patent/ZA825513B/xx unknown
- 1982-07-30 DE DE8282401425T patent/DE3262671D1/de not_active Expired
- 1982-07-30 ZA ZA825512A patent/ZA825512B/xx unknown
- 1982-07-30 DE DE8282401424T patent/DE3269383D1/de not_active Expired
- 1982-07-30 EP EP82401424A patent/EP0074863B1/fr not_active Expired
- 1982-07-30 AT AT82401425T patent/ATE12227T1/de not_active IP Right Cessation
- 1982-07-30 AT AT82401424T patent/ATE18216T1/de not_active IP Right Cessation
- 1982-07-30 EP EP82401425A patent/EP0072726B1/fr not_active Expired
- 1982-08-02 MA MA19773A patent/MA19562A1/fr unknown
- 1982-08-02 MA MA19771A patent/MA19560A1/fr unknown
- 1982-08-03 CS CS825799A patent/CS229940B2/cs unknown
- 1982-08-03 CS CS825800A patent/CS229941B2/cs unknown
- 1982-08-04 EG EG82474A patent/EG15747A/xx active
- 1982-08-04 EG EG473/82A patent/EG15788A/xx active
- 1982-08-06 CA CA000408843A patent/CA1174240A/en not_active Expired
- 1982-08-06 SU SU823476698A patent/SU1140685A3/ru active
- 1982-08-06 PL PL1982237809A patent/PL130647B1/pl unknown
- 1982-08-06 PH PH27679A patent/PH18545A/en unknown
- 1982-08-06 OA OA57767A patent/OA07175A/xx unknown
- 1982-08-06 OA OA57768A patent/OA07176A/xx unknown
- 1982-08-06 ES ES514795A patent/ES8305738A1/es not_active Expired
- 1982-08-06 YU YU01720/82A patent/YU172082A/xx unknown
- 1982-08-06 SU SU823475704A patent/SU1138024A3/ru active
- 1982-08-06 NZ NZ201518A patent/NZ201518A/en unknown
- 1982-08-06 HU HU822542A patent/HU189166B/hu not_active IP Right Cessation
- 1982-08-06 ES ES514794A patent/ES514794A0/es active Granted
- 1982-08-06 YU YU01718/82A patent/YU171882A/xx unknown
- 1982-08-06 DK DK354382A patent/DK148537C/da not_active IP Right Cessation
- 1982-08-06 FI FI822747A patent/FI72968C/fi not_active IP Right Cessation
- 1982-08-06 JP JP57137832A patent/JPS5877867A/ja active Granted
- 1982-08-06 DK DK354482A patent/DK148795C/da not_active IP Right Cessation
- 1982-08-06 NZ NZ201520A patent/NZ201520A/xx unknown
- 1982-08-06 HU HU822545A patent/HU190028B/hu not_active IP Right Cessation
- 1982-08-06 AR AR290243A patent/AR231637A1/es active
- 1982-08-06 JP JP57137833A patent/JPS5877868A/ja active Pending
- 1982-08-06 PL PL1982237808A patent/PL137199B1/pl unknown
- 1982-08-06 AR AR290242A patent/AR231441A1/es active
- 1982-08-06 FI FI822748A patent/FI72969C/fi not_active IP Right Cessation
- 1982-08-06 CA CA000408844A patent/CA1179346A/en not_active Expired
- 1982-08-07 KR KR8203558A patent/KR880001624B1/ko not_active Expired
- 1982-08-07 KR KR8203557A patent/KR890001569B1/ko not_active Expired
- 1982-08-09 DD DD82242356A patent/DD202715A5/de unknown
- 1982-08-09 DD DD82242359A patent/DD202549A5/de unknown
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