NO751350L - - Google Patents
Info
- Publication number
- NO751350L NO751350L NO751350A NO751350A NO751350L NO 751350 L NO751350 L NO 751350L NO 751350 A NO751350 A NO 751350A NO 751350 A NO751350 A NO 751350A NO 751350 L NO751350 L NO 751350L
- Authority
- NO
- Norway
- Prior art keywords
- urea
- oxo
- cyclohexen
- compounds
- approx
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 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 description 3
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 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 description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 claims description 2
- SOPWCEFXKLAPKS-UHFFFAOYSA-N (1-methylcyclopentyl)urea Chemical compound NC(=O)NC1(C)CCCC1 SOPWCEFXKLAPKS-UHFFFAOYSA-N 0.000 claims 1
- NYVOTEXDOXBFPM-UHFFFAOYSA-N (3-oxocyclohexen-1-yl)urea Chemical compound O=C1C=C(CCC1)NC(=O)N NYVOTEXDOXBFPM-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 8
- 206010020772 Hypertension Diseases 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 230000001631 hypertensive effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 239000002220 antihypertensive agent Substances 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229940030600 antihypertensive agent Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229960004486 desoxycorticosterone acetate Drugs 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000004873 systolic arterial blood pressure Effects 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 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 description 1
- CVNWTAXWQHMONY-UHFFFAOYSA-N 2-tert-butylguanidine Chemical class CC(C)(C)NC(N)=N CVNWTAXWQHMONY-UHFFFAOYSA-N 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- VZVGEDRCVUKSEL-UHFFFAOYSA-N guancidine Chemical compound CCC(C)(C)N=C(N)NC#N VZVGEDRCVUKSEL-UHFFFAOYSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- -1 hexen-1-yl Chemical group 0.000 description 1
- 230000009097 homeostatic mechanism Effects 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Dispersion Chemistry (AREA)
- Birds (AREA)
- Biochemistry (AREA)
- Molecular Biology (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 |
|---|---|
| NO751350L true NO751350L (US07993877-20110809-P00003.png) | 1975-10-20 |
Family
ID=27412847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO751350A NO751350L (US07993877-20110809-P00003.png) | 1974-04-17 | 1975-04-16 |
Country Status (18)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2424162A1 (fr) * | 1978-04-24 | 1979-11-23 | British Hovercraft Corp Ltd | Perfectionnements aux jupes de vehicules a coussins d'air |
| 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 |
| EP0278907B1 (de) * | 1987-02-09 | 1991-05-29 | 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 GB GB1567075A patent/GB1457245A/en 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 ES ES436647A patent/ES436647A1/es not_active Expired
- 1975-04-16 DK DK163975AA patent/DK134318B/da not_active IP Right Cessation
- 1975-04-16 FI FI751127A patent/FI751127A/fi not_active Application Discontinuation
- 1975-04-16 DE DE19752516556 patent/DE2516556A1/de not_active Withdrawn
- 1975-04-16 PH PH17060A patent/PH11869A/en unknown
- 1975-04-16 NO NO751350A patent/NO751350L/no unknown
- 1975-04-17 IE IE864/75A patent/IE40999B1/xx unknown
- 1975-04-17 JP JP50045923A patent/JPS50148337A/ja active Pending
- 1975-04-17 CH CH494775A patent/CH611273A5/xx not_active IP Right Cessation
- 1975-04-17 LU LU72305A patent/LU72305A1/xx unknown
- 1975-04-17 NL NL7504568A patent/NL7504568A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL47097A0 (en) | 1975-06-25 |
| AU8013475A (en) | 1976-10-21 |
| DD119223A5 (US07993877-20110809-P00003.png) | 1976-04-12 |
| PH11869A (en) | 1978-08-04 |
| FR2267766A1 (US07993877-20110809-P00003.png) | 1975-11-14 |
| DK163975A (US07993877-20110809-P00003.png) | 1975-10-18 |
| DE2516556A1 (de) | 1975-10-30 |
| IE40999L (en) | 1975-10-17 |
| SE7503522L (sv) | 1975-10-20 |
| JPS50148337A (US07993877-20110809-P00003.png) | 1975-11-27 |
| FR2267766B1 (US07993877-20110809-P00003.png) | 1978-10-06 |
| NL7504568A (nl) | 1975-10-21 |
| CH611273A5 (en) | 1979-05-31 |
| LU72305A1 (US07993877-20110809-P00003.png) | 1976-03-17 |
| FI751127A (US07993877-20110809-P00003.png) | 1975-10-18 |
| DK134318B (da) | 1976-10-18 |
| GB1457245A (en) | 1976-12-01 |
| IE40999B1 (en) | 1979-09-26 |
| CA1051029A (en) | 1979-03-20 |
| AR206020A1 (es) | 1976-06-23 |
| IL47097A (en) | 1978-03-10 |
| ES436647A1 (es) | 1977-08-01 |
| DK134318C (US07993877-20110809-P00003.png) | 1977-04-18 |
| SE398116B (sv) | 1977-12-05 |
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