FR2528837A1 - Arylacetyl butanolides et leurs derives pyridazinones utilisables comme medicaments, et procedes pour leur fabrication - Google Patents
Arylacetyl butanolides et leurs derives pyridazinones utilisables comme medicaments, et procedes pour leur fabrication Download PDFInfo
- Publication number
- FR2528837A1 FR2528837A1 FR8210630A FR8210630A FR2528837A1 FR 2528837 A1 FR2528837 A1 FR 2528837A1 FR 8210630 A FR8210630 A FR 8210630A FR 8210630 A FR8210630 A FR 8210630A FR 2528837 A1 FR2528837 A1 FR 2528837A1
- Authority
- FR
- France
- Prior art keywords
- pyridazinone
- och
- derivatives
- compounds
- new
- 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.)
- Granted
Links
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000001624 sedative effect Effects 0.000 claims abstract description 5
- 239000002841 Lewis acid Substances 0.000 claims abstract description 4
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 4
- 238000009833 condensation Methods 0.000 claims abstract description 3
- 230000005494 condensation Effects 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 7
- -1 acyl butanolide Chemical compound 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 239000002547 new drug Substances 0.000 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001299 aldehydes Chemical class 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- 239000002775 capsule Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 210000000748 cardiovascular system Anatomy 0.000 description 3
- 230000000004 hemodynamic effect Effects 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- BGLUXFNVVSVEET-UHFFFAOYSA-N beta-angelica lactone Chemical compound CC1OC(=O)C=C1 BGLUXFNVVSVEET-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 238000007914 intraventricular administration Methods 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- SSDAKJLEKSSAMH-UHFFFAOYSA-N 2,4-dihydro-1h-pyridazin-3-one Chemical compound O=C1CC=CNN1 SSDAKJLEKSSAMH-UHFFFAOYSA-N 0.000 description 1
- ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 description 1
- JRIZMXAHUIDMMH-UHFFFAOYSA-N 4-acetyl-5-phenyloxolan-2-one Chemical compound CC(=O)C1CC(=O)OC1C1=CC=CC=C1 JRIZMXAHUIDMMH-UHFFFAOYSA-N 0.000 description 1
- QRHUVHQLBCIWST-UHFFFAOYSA-N 5-(hydroxymethyl)-1h-pyridazin-6-one Chemical compound OCC1=CC=NNC1=O QRHUVHQLBCIWST-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 206010005746 Blood pressure fluctuation Diseases 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 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 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000406668 Loxodonta cyclotis Species 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000004646 arylidenes Chemical class 0.000 description 1
- 229960000796 barbital sodium Drugs 0.000 description 1
- FTOAOBMCPZCFFF-UHFFFAOYSA-N barbitone sodium Natural products CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RGHFKWPGWBFQLN-UHFFFAOYSA-M sodium;5,5-diethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CCC1(CC)C([O-])=NC(=O)NC1=O RGHFKWPGWBFQLN-UHFFFAOYSA-M 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8210630A FR2528837A1 (fr) | 1982-06-18 | 1982-06-18 | Arylacetyl butanolides et leurs derives pyridazinones utilisables comme medicaments, et procedes pour leur fabrication |
| CH320483A CH657125B (enrdf_load_stackoverflow) | 1982-06-18 | 1983-06-10 | |
| NL8302087A NL8302087A (nl) | 1982-06-18 | 1983-06-11 | Pyridazinonverbindingen, werkwijze voor de bereiding hiervan en de toepassing als geneesmiddel. |
| GR71641A GR78284B (enrdf_load_stackoverflow) | 1982-06-18 | 1983-06-13 | |
| DE3321772A DE3321772A1 (de) | 1982-06-18 | 1983-06-16 | Pyridazinon-derivate, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
| IT8321684A IT1194281B (it) | 1982-06-18 | 1983-06-17 | Derivati di piridazinoni impiegabili come sostanze medicinali e procedimento per la loro fabricazione |
| KR1019830002710A KR860001339B1 (ko) | 1982-06-18 | 1983-06-17 | 피리다지논 유도체의 제조방법 |
| BE0/211031A BE897085A (fr) | 1982-06-18 | 1983-06-17 | Derives de pyridazinones utilisables comme medicaments et procedes pour leur fabrication |
| JP58108026A JPS5910571A (ja) | 1982-06-18 | 1983-06-17 | 医薬品として使用可能なピリダジノンの誘導体、及びそれの製造方法 |
| GB08316516A GB2122195A (en) | 1982-06-18 | 1983-06-17 | Pyridazinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8210630A FR2528837A1 (fr) | 1982-06-18 | 1982-06-18 | Arylacetyl butanolides et leurs derives pyridazinones utilisables comme medicaments, et procedes pour leur fabrication |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2528837A1 true FR2528837A1 (fr) | 1983-12-23 |
| FR2528837B1 FR2528837B1 (enrdf_load_stackoverflow) | 1984-12-07 |
Family
ID=9275129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8210630A Granted FR2528837A1 (fr) | 1982-06-18 | 1982-06-18 | Arylacetyl butanolides et leurs derives pyridazinones utilisables comme medicaments, et procedes pour leur fabrication |
Country Status (10)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129791A3 (de) * | 1983-06-20 | 1987-06-10 | CASSELLA Aktiengesellschaft | Tetrahydropyridazinonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0210530A1 (de) * | 1985-07-27 | 1987-02-04 | MERCK PATENT GmbH | 6-Arylalkenylpyridazinone |
| JPS63220512A (ja) * | 1987-03-09 | 1988-09-13 | 松下電器産業株式会社 | 電解コンデンサ用電極箔 |
| JPH04100106U (enrdf_load_stackoverflow) * | 1991-02-12 | 1992-08-28 | ||
| JPH0776050B2 (ja) * | 1991-07-25 | 1995-08-16 | 実 近藤 | ワークの移送装置 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2304977A1 (de) * | 1973-02-01 | 1974-08-08 | Basf Ag | Neue dihydropyridazinone |
-
1982
- 1982-06-18 FR FR8210630A patent/FR2528837A1/fr active Granted
-
1983
- 1983-06-10 CH CH320483A patent/CH657125B/fr not_active IP Right Cessation
- 1983-06-11 NL NL8302087A patent/NL8302087A/nl not_active Application Discontinuation
- 1983-06-13 GR GR71641A patent/GR78284B/el unknown
- 1983-06-16 DE DE3321772A patent/DE3321772A1/de not_active Withdrawn
- 1983-06-17 IT IT8321684A patent/IT1194281B/it active
- 1983-06-17 GB GB08316516A patent/GB2122195A/en not_active Withdrawn
- 1983-06-17 JP JP58108026A patent/JPS5910571A/ja active Pending
- 1983-06-17 BE BE0/211031A patent/BE897085A/fr not_active IP Right Cessation
- 1983-06-17 KR KR1019830002710A patent/KR860001339B1/ko not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2304977A1 (de) * | 1973-02-01 | 1974-08-08 | Basf Ag | Neue dihydropyridazinone |
Non-Patent Citations (3)
| Title |
|---|
| BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, volume 49, no. 4, avril 1976 (TOKYO, JP) T. SATO et al. "A convenient synthesis of beta-acetyl-gamma-substituted-gamma-butyrolactones and gamma-acetyl-delta-substituted-delta-valerolactones", pages 1055-1058 * |
| CHEMICAL ABSTRACTS, volume 72, no. 2, 12 janvier 1970, page 458, abrégé 9048r (COLUMBUS OHIO, US) & Suom. Kemistilehti B 1969, 42(7-8), 312-13, S. ESKOLA et al. "Thin-layer chromatographic study of some 3-methyl-6-pyridazinone derivatives" * |
| CHEMICAL ABSTRACTS, volume 95, no. 23, 7 décembre 1981, page 50, abrégé 197388y (COLUMBUS OHIO, US) & Ann. Pharm. Fr. 1981, 39(3), 215-22, PHAM HUU CHANH et al. "Cardiostimulant action and hemodynamic effects of a new beta-acetyl butyrolactone" * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129791A3 (de) * | 1983-06-20 | 1987-06-10 | CASSELLA Aktiengesellschaft | Tetrahydropyridazinonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| BE897085A (fr) | 1983-12-19 |
| IT1194281B (it) | 1988-09-14 |
| NL8302087A (nl) | 1984-01-16 |
| FR2528837B1 (enrdf_load_stackoverflow) | 1984-12-07 |
| IT8321684A0 (it) | 1983-06-17 |
| GR78284B (enrdf_load_stackoverflow) | 1984-09-26 |
| GB2122195A (en) | 1984-01-11 |
| CH657125B (enrdf_load_stackoverflow) | 1986-08-15 |
| JPS5910571A (ja) | 1984-01-20 |
| KR840005105A (ko) | 1984-11-03 |
| DE3321772A1 (de) | 1983-12-22 |
| GB8316516D0 (en) | 1983-07-20 |
| KR860001339B1 (ko) | 1986-09-15 |
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