CA1051029A - Cyclohexenyl compounds - Google Patents
Cyclohexenyl compoundsInfo
- Publication number
- CA1051029A CA1051029A CA224,635A CA224635A CA1051029A CA 1051029 A CA1051029 A CA 1051029A CA 224635 A CA224635 A CA 224635A CA 1051029 A CA1051029 A CA 1051029A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- urea
- formula
- tert
- oxo
- 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
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- YDIFANJGYCFZIU-UHFFFAOYSA-N 1-tert-butyl-3-(3-oxocyclohexen-1-yl)urea Chemical compound CC(C)(C)NC(=O)NC1=CC(=O)CCC1 YDIFANJGYCFZIU-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- KOAIQFUGRGGACC-UHFFFAOYSA-N 1-(1-methylcyclopentyl)-3-(3-oxocyclohexen-1-yl)urea Chemical compound C=1C(=O)CCCC=1NC(=O)NC1(C)CCCC1 KOAIQFUGRGGACC-UHFFFAOYSA-N 0.000 claims 1
- XRNUYTBHTFJIPB-UHFFFAOYSA-N 1-(2-methylbutan-2-yl)-3-(3-oxocyclohexen-1-yl)urea Chemical compound CCC(C)(C)NC(=O)NC1=CC(=O)CCC1 XRNUYTBHTFJIPB-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 6
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 150000003672 ureas Chemical class 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 239000004202 carbamide Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000003937 drug carrier Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 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 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 oxo-1 cyclohexen-l-yl Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- NYVOTEXDOXBFPM-UHFFFAOYSA-N (3-oxocyclohexen-1-yl)urea Chemical compound O=C1C=C(CCC1)NC(=O)N NYVOTEXDOXBFPM-UHFFFAOYSA-N 0.000 description 1
- NOOUGSSBMSGVBY-UHFFFAOYSA-N 1-butyl-3-(3-oxocyclohexen-1-yl)urea Chemical compound C(CCC)NC(=O)NC1=CC(CCC1)=O NOOUGSSBMSGVBY-UHFFFAOYSA-N 0.000 description 1
- CVNWTAXWQHMONY-UHFFFAOYSA-N 2-tert-butylguanidine Chemical compound CC(C)(C)NC(N)=N CVNWTAXWQHMONY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- 241000459479 Capsula Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 101000973623 Homo sapiens Neuronal growth regulator 1 Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 102100022223 Neuronal growth regulator 1 Human genes 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 235000015220 hamburgers Nutrition 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/26—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46169774A | 1974-04-17 | 1974-04-17 | |
| US52544574A | 1974-11-20 | 1974-11-20 | |
| US05/555,308 US4002767A (en) | 1974-11-20 | 1975-03-11 | 1-Tertiary-alkyl-3-(substituted cyclohexenyl)ureas as antihypertensive agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051029A true CA1051029A (en) | 1979-03-20 |
Family
ID=27412847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA224,635A Expired CA1051029A (en) | 1974-04-17 | 1975-04-15 | Cyclohexenyl compounds |
Country Status (18)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54151218A (en) * | 1978-04-24 | 1979-11-28 | British Hovercraft Corp Ltd | Split preventive device |
| EP0004959A1 (de) * | 1978-04-24 | 1979-10-31 | Ciba-Geigy Ag | Verfahren zur Herstellung von 3-Oxo-cyclopentenylharnstoffen, die so erhaltenen Verbindungen, sie enthaltende pharmazeutische Präparate und 3-Oxo-cyclopentenylisothioharnstoffe |
| DE3862944D1 (de) * | 1987-02-09 | 1991-07-04 | Ciba Geigy Ag | Neue cyclohexandione. |
-
1975
- 1975-01-01 AR AR258395A patent/AR206020A1/es active
- 1975-03-26 SE SE7503522A patent/SE398116B/xx not_active IP Right Cessation
- 1975-04-15 IL IL47097A patent/IL47097A/xx unknown
- 1975-04-15 CA CA224,635A patent/CA1051029A/en not_active Expired
- 1975-04-16 PH PH17060A patent/PH11869A/en unknown
- 1975-04-16 DK DK163975AA patent/DK134318B/da not_active IP Right Cessation
- 1975-04-16 ES ES436647A patent/ES436647A1/es not_active Expired
- 1975-04-16 FR FR7511794A patent/FR2267766B1/fr not_active Expired
- 1975-04-16 DD DD185481A patent/DD119223A5/xx unknown
- 1975-04-16 NO NO751350A patent/NO751350L/no unknown
- 1975-04-16 FI FI751127A patent/FI751127A7/fi not_active Application Discontinuation
- 1975-04-16 GB GB1567075A patent/GB1457245A/en not_active Expired
- 1975-04-16 DE DE19752516556 patent/DE2516556A1/de not_active Withdrawn
- 1975-04-17 NL NL7504568A patent/NL7504568A/xx not_active Application Discontinuation
- 1975-04-17 LU LU72305A patent/LU72305A1/xx unknown
- 1975-04-17 JP JP50045923A patent/JPS50148337A/ja active Pending
- 1975-04-17 IE IE864/75A patent/IE40999B1/xx unknown
- 1975-04-17 CH CH494775A patent/CH611273A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH611273A5 (en) | 1979-05-31 |
| AR206020A1 (es) | 1976-06-23 |
| IE40999B1 (en) | 1979-09-26 |
| IE40999L (en) | 1975-10-17 |
| AU8013475A (en) | 1976-10-21 |
| FR2267766A1 (enrdf_load_stackoverflow) | 1975-11-14 |
| DK134318C (enrdf_load_stackoverflow) | 1977-04-18 |
| DE2516556A1 (de) | 1975-10-30 |
| SE398116B (sv) | 1977-12-05 |
| IL47097A (en) | 1978-03-10 |
| DD119223A5 (enrdf_load_stackoverflow) | 1976-04-12 |
| DK163975A (enrdf_load_stackoverflow) | 1975-10-18 |
| DK134318B (da) | 1976-10-18 |
| PH11869A (en) | 1978-08-04 |
| SE7503522L (sv) | 1975-10-20 |
| NL7504568A (nl) | 1975-10-21 |
| ES436647A1 (es) | 1977-08-01 |
| FR2267766B1 (enrdf_load_stackoverflow) | 1978-10-06 |
| JPS50148337A (enrdf_load_stackoverflow) | 1975-11-27 |
| GB1457245A (en) | 1976-12-01 |
| FI751127A7 (enrdf_load_stackoverflow) | 1975-10-18 |
| NO751350L (enrdf_load_stackoverflow) | 1975-10-20 |
| LU72305A1 (enrdf_load_stackoverflow) | 1976-03-17 |
| IL47097A0 (en) | 1975-06-25 |
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