SK70895A3 - Fatty acid derivatives and pharmaceutical compositions containing them - Google Patents

Fatty acid derivatives and pharmaceutical compositions containing them Download PDF

Info

Publication number: SK70895A3
Authority: SK; Slovakia
Prior art keywords: compound according; compounds; anandamide; small; group
Prior art date: 1992-11-30

Application number

SK708-95A

Other languages

English (en)

Slovak (sk)

Inventor

Raphael Mechoulam

Aviva Beuer

Lumir Hanus

William A Devane

Original Assignee

Yissum Research Devel Of The H

Priority date (The priority date 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 date listed.)

1992-11-30

Filing date

1993-11-30

Publication date

1995-09-13

1993-11-30 Application filed by Yissum Research Devel Of The H filed Critical Yissum Research Devel Of The H

1995-09-13 Publication of SK70895A3 publication Critical patent/SK70895A3/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
229940053200 antiepileptics fatty acid derivative Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 51
210000004556 brain Anatomy 0.000 claims abstract description 20
102000018208 Cannabinoid Receptor Human genes 0.000 claims abstract description 9
108050007331 Cannabinoid receptor Proteins 0.000 claims abstract description 9
239000004480 active ingredient Substances 0.000 claims abstract description 6
235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 6
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 4
LGEQQWMQCRIYKG-DOFZRALJSA-N anandamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO LGEQQWMQCRIYKG-DOFZRALJSA-N 0.000 claims description 36
230000027455 binding Effects 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 6
230000001384 anti-glaucoma Effects 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
230000000202 analgesic effect Effects 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
-1 analgesic Substances 0.000 claims description 4
230000003110 anti-inflammatory effect Effects 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
230000003474 anti-emetic effect Effects 0.000 claims description 3
230000001088 anti-asthma Effects 0.000 claims description 2
230000002460 anti-migrenic effect Effects 0.000 claims description 2
230000001663 anti-spastic effect Effects 0.000 claims description 2
239000000924 antiasthmatic agent Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
230000036651 mood Effects 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
208000024891 symptom Diseases 0.000 claims description 2
WHUHTCSYMDOIGU-FNORWQNLSA-N (3e)-octadeca-1,3-diene Chemical compound CCCCCCCCCCCCCC\C=C\C=C WHUHTCSYMDOIGU-FNORWQNLSA-N 0.000 claims 1
YLFLZSQBPHMIBS-UHFFFAOYSA-N N-propylicosa-5,8,11,14-tetraenamide Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCC YLFLZSQBPHMIBS-UHFFFAOYSA-N 0.000 claims 1
239000002111 antiemetic agent Substances 0.000 claims 1
MAMJNXVNGGBHFN-UHFFFAOYSA-N docosa-1,3,5,7,9,11-hexaene Chemical compound CCCCCCCCCCC=CC=CC=CC=CC=CC=C MAMJNXVNGGBHFN-UHFFFAOYSA-N 0.000 claims 1
DCUXLBLUWUQKFU-UHFFFAOYSA-N n-ethylicosa-5,8,11,14-tetraenamide Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCC DCUXLBLUWUQKFU-UHFFFAOYSA-N 0.000 claims 1
HTAWYBRCXMQDBL-UHFFFAOYSA-N n-methylicosa-5,8,11,14-tetraenamide Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC HTAWYBRCXMQDBL-UHFFFAOYSA-N 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 5
208000010412 Glaucoma Diseases 0.000 abstract description 3
230000001766 physiological effect Effects 0.000 abstract description 3
206010061218 Inflammation Diseases 0.000 abstract description 2
208000019695 Migraine disease Diseases 0.000 abstract description 2
230000004054 inflammatory process Effects 0.000 abstract description 2
208000008238 Muscle Spasticity Diseases 0.000 abstract 1
230000003278 mimic effect Effects 0.000 abstract 1
208000018198 spasticity Diseases 0.000 abstract 1
LGEQQWMQCRIYKG-UHFFFAOYSA-N arachidonic acid ethanolamide Natural products CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO LGEQQWMQCRIYKG-UHFFFAOYSA-N 0.000 description 31
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 13
229930003827 cannabinoid Natural products 0.000 description 11
239000003557 cannabinoid Substances 0.000 description 11
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 11
102000005962 receptors Human genes 0.000 description 11
108020003175 receptors Proteins 0.000 description 11
230000005764 inhibitory process Effects 0.000 description 8
229940114079 arachidonic acid Drugs 0.000 description 7
239000012528 membrane Substances 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
235000021342 arachidonic acid Nutrition 0.000 description 6
210000002683 foot Anatomy 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000000034 method Methods 0.000 description 6
230000004044 response Effects 0.000 description 6
BWVILEDUVPUTSY-UHFFFAOYSA-N 1-amino-2-hydroxytetracosa-4,6,8,10-tetraen-3-one Chemical class CCCCCCCCCCCCCC=CC=CC=CC=CC(=O)C(O)CN BWVILEDUVPUTSY-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
238000003556 assay Methods 0.000 description 5
HXYVTAGFYLMHSO-UHFFFAOYSA-N palmitoyl ethanolamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCCO HXYVTAGFYLMHSO-UHFFFAOYSA-N 0.000 description 5
230000009870 specific binding Effects 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229940065144 cannabinoids Drugs 0.000 description 4
CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
230000004410 intraocular pressure Effects 0.000 description 4
229950007031 palmidrol Drugs 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 3
206010047700 Vomiting Diseases 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
239000003446 ligand Substances 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000002287 radioligand Substances 0.000 description 3
239000000523 sample Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000272201 Columbiformes Species 0.000 description 2
206010010904 Convulsion Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
125000000746 allylic group Chemical group 0.000 description 2
230000036592 analgesia Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
230000006957 competitive inhibition Effects 0.000 description 2
230000002920 convulsive effect Effects 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000013467 fragmentation Methods 0.000 description 2
238000006062 fragmentation reaction Methods 0.000 description 2
230000006870 function Effects 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000005040 ion trap Methods 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
235000015277 pork Nutrition 0.000 description 2
230000000506 psychotropic effect Effects 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
210000001177 vas deferen Anatomy 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
230000008673 vomiting Effects 0.000 description 2
QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
NTBLHFFUSJRJQO-DOFZRALJSA-N (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoyl chloride Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(Cl)=O NTBLHFFUSJRJQO-DOFZRALJSA-N 0.000 description 1
LOUSQMWLMDHRIK-IAGOWNOFSA-N (6ar,10ar)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol Chemical compound C1C(CO)=CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 LOUSQMWLMDHRIK-IAGOWNOFSA-N 0.000 description 1
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
241000218236 Cannabis Species 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
108091006027 G proteins Proteins 0.000 description 1
102000030782 GTP binding Human genes 0.000 description 1
108091000058 GTP-Binding Proteins 0.000 description 1
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
KWKZCGMJGHHOKJ-ZKWNWVNESA-N Methyl Arachidonyl Fluorophosphonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCP(F)(=O)OC KWKZCGMJGHHOKJ-ZKWNWVNESA-N 0.000 description 1
241001529936 Murinae Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000000540 analysis of variance Methods 0.000 description 1
210000003423 ankle Anatomy 0.000 description 1
230000000118 anti-neoplastic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
210000000133 brain stem Anatomy 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
229960002376 chymotrypsin Drugs 0.000 description 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000009137 competitive binding Effects 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229960004242 dronabinol Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000008451 emotion Effects 0.000 description 1
239000006274 endogenous ligand Substances 0.000 description 1
239000012634 fragment Substances 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
JYLZAJNZMATBKX-UHFFFAOYSA-N icosa-6,9,12-triene Chemical compound CCCCCCCC=CCC=CCC=CCCCCC JYLZAJNZMATBKX-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002617 leukotrienes Chemical class 0.000 description 1
235000020778 linoleic acid Nutrition 0.000 description 1
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
125000003473 lipid group Chemical group 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
230000004807 localization Effects 0.000 description 1
230000033001 locomotion Effects 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000015654 memory Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
229960004127 naloxone Drugs 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
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
230000036407 pain Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229960001416 pilocarpine Drugs 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
238000003653 radioligand binding assay Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000001148 spastic effect Effects 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/20—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Ophthalmology & Optometry (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK708-95A 1992-11-30 1993-11-30 Fatty acid derivatives and pharmaceutical compositions containing them SK70895A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IL10393292A IL103932A (en)	1992-11-30	1992-11-30	Fatty acid and pharmaceutical compositions containing them
PCT/US1993/011625 WO1994012466A1 (en)	1992-11-30	1993-11-30	Fatty acid derivatives and pharmaceutical compositions containing them

Publications (1)

Publication Number	Publication Date
SK70895A3 true SK70895A3 (en)	1995-09-13

Family

ID=11064282

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK708-95A SK70895A3 (en)	1992-11-30	1993-11-30	Fatty acid derivatives and pharmaceutical compositions containing them

Country Status (13)

Country	Link
EP (1)	EP0670826B1 (de)
JP (1)	JPH08504195A (de)
CN (1)	CN1097735A (de)
AU (1)	AU5733494A (de)
CZ (1)	CZ136195A3 (de)
DE (1)	DE69328492T2 (de)
ES (1)	ES2145118T3 (de)
HU (1)	HUT73177A (de)
IL (1)	IL103932A (de)
PL (1)	PL309051A1 (de)
SK (1)	SK70895A3 (de)
WO (1)	WO1994012466A1 (de)
ZA (1)	ZA938947B (de)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5631297A (en) *	1994-07-11	1997-05-20	Pate; David W.	Anandamides useful for the treatment of intraocular hypertension, ophthalmic compositions containing the same and methods of use of the same
CA2192965C (en) *	1994-07-11	2007-12-04	David W. Pate	Anandamide analogue compositions and method of treating intraocular hypertension using same
IT1271267B (it) *	1994-12-14	1997-05-27	Valle Francesco Della	Ammidi di acidi mono e bicarbossilici con amminoalcoli,selettivamente attive sul recettore periferico dei cannabinoidi
DE19544635A1 (de) *	1995-11-30	1997-06-05	Boehringer Mannheim Gmbh	Neue Aminoalkoholderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE19706903A1 (de) *	1997-02-21	1998-08-27	Bayer Ag	Verwendung von bekannten Agonisten des zentralen Cannabinoid-Rezeptors CB 1
AU765670B2 (en)	1998-04-03	2003-09-25	Yissum Research Development Company Of The Hebrew University Of Jerusalem	Synthetic endogenous cannabinoids analogues and uses thereof
EP1645270B1 (de) *	1998-05-29	2010-04-28	Neurosciences Research Foundation Inc.	Schmerzlinderung mit anandamide
US7897598B2 (en)	1998-06-09	2011-03-01	Alexandros Makriyannis	Inhibitors of the anandamide transporter
US7589220B2 (en)	1998-06-09	2009-09-15	University Of Connecticut	Inhibitors of the anandamide transporter
CA2307285C (en)	1998-08-17	2009-03-31	Senju Pharmaceutical Co., Ltd.	Agent for prophylaxis and treatment of glaucoma
US7276613B1 (en)	1998-11-24	2007-10-02	University Of Connecticut	Retro-anandamides, high affinity and stability cannabinoid receptor ligands
US7161016B1 (en)	1998-11-24	2007-01-09	University Of Connecticut	Cannabimimetic lipid amides as useful medications
EP1049474A4 (de) *	1998-11-24	2004-12-29	Univ Connecticut	Cannabimimetische lipidamide als arzneimittel
GB9923738D0 (en) *	1999-10-07	1999-12-08	Nestle Sa	Nutritional composition
US7393842B2 (en)	2001-08-31	2008-07-01	University Of Connecticut	Pyrazole analogs acting on cannabinoid receptors
US6900236B1 (en)	1999-10-18	2005-05-31	University Of Connecticut	Cannabimimetic indole derivatives
US6943266B1 (en)	1999-10-18	2005-09-13	University Of Connecticut	Bicyclic cannabinoid agonists for the cannabinoid receptor
US7119108B1 (en)	1999-10-18	2006-10-10	University Of Connecticut	Pyrazole derivatives as cannabinoid receptor antagonists
CA2410401A1 (en)	2000-05-23	2001-11-29	Daniele Piomelli	A novel treatment for cough
NO20006008L (no)	2000-11-28	2002-05-29	Thia Medica As	Fettsyreanaloger for behandling av inflammatoriske og autoimmune sykdommer
US8449908B2 (en)	2000-12-22	2013-05-28	Alltranz, Llc	Transdermal delivery of cannabidiol
EP1361876A4 (de)	2001-01-26	2004-03-31	Univ Connecticut	Neue cannabimimetische liganden
IL158131A0 (en)	2001-03-27	2004-03-28	Univ California	Methods, compounds, and compositions for reducing body fat and modulating fatty acid metabolism
JP4312594B2 (ja)	2001-07-13	2009-08-12	ユニバーシティオブコネチカット	新規な二環式及び三環式カンナビノイド
WO2003008632A1 (en) *	2001-07-16	2003-01-30	Hoegestaett Edward	Fatty acid conjugation as a method for screening of potentially bioactive substances
WO2003075917A1 (en)	2002-03-08	2003-09-18	Signal Pharmaceuticals, Inc.	Combination therapy for treating, preventing or managing proliferative disorders and cancers
DE60320784D1 (de)	2002-06-06	2008-06-19	Yissum Res Dev Co	Stände zur modulierung des knochenwachstums
ITMI20030210A1 (it) *	2003-02-07	2004-08-08	Res & Innovation Soc Coop A R L	Composti endocannabinoido-simili e loro impiego
WO2005007628A1 (en)	2003-07-11	2005-01-27	Bristol-Myers Squibb Company	Tetrahydroquinoline derivatives as cannabinoid receptor modulators
US7326706B2 (en)	2003-08-15	2008-02-05	Bristol-Myers Squibb Company	Pyrazine modulators of cannabinoid receptors
IL160420A0 (en)	2004-02-16	2004-07-25	Yissum Res Dev Co	Treating or preventing diabetes with cannabidiol
JP2009538827A (ja) *	2006-05-01	2009-11-12	イースタンバージニアメディカルスクール	カンナビノイドおよび使用方法
US20080175902A1 (en) *	2006-11-30	2008-07-24	University Of Plymouth	Methods for slowing the progression of multiple sclerosis
DK2176208T3 (en)	2007-07-30	2015-04-27	Zynerba Pharmaceuticals Inc	Prodrugs of cannabidiol, compositions containing prodrugs of cannabidiol and methods of use thereof
US20110178151A1 (en)	2008-03-04	2011-07-21	Yissum Research Development Company Of The Hebrew	Compounds and methods of treating obesity
US9623000B2 (en)	2008-07-31	2017-04-18	Dekel Pharmaceuticals Ltd	Compositions and methods for treating inflammatory disorders
EP2504311B1 (de) *	2009-11-25	2015-08-12	Cytometix, Inc.	Arachidonsäureanaloga und verfahren zur schmerzbehandlung damit
CN103877100B (zh) *	2013-05-21	2016-08-10	成都旗美健康食品有限公司	亚麻酸酰基乙醇胺的联合医用和保健用药物
WO2020214569A1 (en) *	2019-04-15	2020-10-22	Metagenics, Inc.	Novel hemp and pea formulation and its use

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE306730B (de) *	1963-02-06	1968-12-09	Sumitomo Chemical Co
SE353319B (de) *	1964-08-15	1973-01-29	Sumitomo Chemical Co
US4619938A (en) *	1984-03-21	1986-10-28	Terumo Kabushiki Kaisha	Fatty acid derivatives of aminoalkyl nicotinic acid esters and platelet aggregation inhibitors
FR2584400B1 (fr) *	1985-07-05	1988-02-19	Cird	Esters et amides de l'acide eicosatriynoique et leur application en pharmacie et en cosmetique

1992
- 1992-11-30 IL IL10393292A patent/IL103932A/xx not_active IP Right Cessation
1993
- 1993-11-30 DE DE69328492T patent/DE69328492T2/de not_active Expired - Fee Related
- 1993-11-30 AU AU57334/94A patent/AU5733494A/en not_active Abandoned
- 1993-11-30 EP EP94903364A patent/EP0670826B1/de not_active Expired - Lifetime
- 1993-11-30 PL PL93309051A patent/PL309051A1/xx unknown
- 1993-11-30 CZ CZ951361A patent/CZ136195A3/cs unknown
- 1993-11-30 SK SK708-95A patent/SK70895A3/sk unknown
- 1993-11-30 ES ES94903364T patent/ES2145118T3/es not_active Expired - Lifetime
- 1993-11-30 CN CN93121715A patent/CN1097735A/zh active Pending
- 1993-11-30 HU HU9501561A patent/HUT73177A/hu unknown
- 1993-11-30 WO PCT/US1993/011625 patent/WO1994012466A1/en not_active Ceased
- 1993-11-30 JP JP6513466A patent/JPH08504195A/ja active Pending
- 1993-11-30 ZA ZA938947A patent/ZA938947B/xx unknown

Also Published As

Publication number	Publication date
ES2145118T3 (es)	2000-07-01
IL103932A0 (en)	1993-04-04
HUT73177A (en)	1996-06-28
EP0670826A4 (de)	1996-08-14
PL309051A1 (en)	1995-09-18
AU5733494A (en)	1994-06-22
DE69328492D1 (de)	2000-05-31
EP0670826A1 (de)	1995-09-13
JPH08504195A (ja)	1996-05-07
HU9501561D0 (en)	1995-07-28
CN1097735A (zh)	1995-01-25
WO1994012466A1 (en)	1994-06-09
IL103932A (en)	1997-02-18
EP0670826B1 (de)	2000-04-26
CZ136195A3 (en)	1995-11-15
ZA938947B (en)	1994-08-02
DE69328492T2 (de)	2000-09-07

Publication	Publication Date	Title
SK70895A3 (en)	1995-09-13	Fatty acid derivatives and pharmaceutical compositions containing them
US5618955A (en)	1997-04-08	Fatty acid derivatives and pharmaceutical compositions containing same
Hanus et al.	1993	Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor
US4479932A (en)	1984-10-30	Brain-specific drug delivery
Shelley et al.	2000	Structure-activity studies on gossypol in tumor cell lines
US5021450A (en)	1991-06-04	New class of compounds having a variable spectrum of activities for capsaicin-like responses, compositions and uses thereof
Cai et al.	2005	Methyl palmitate: inhibitor of phagocytosis in primary rat Kupffer cells
AU5622598A (en)	1998-07-31	Brain targeted low molecular weight hydrophobic antioxidant compounds
Bodor et al.	1988	Soft drugs. 7. Soft. beta.-blockers for systemic and ophthalmic use
US5869714A (en)	1999-02-09	Salts of omega-3-polyunsaturated fatty acids and pharmaceutical formulations containing them
Jacob et al.	1990	Synthesis, brain uptake, and pharmacological properties of a glyceryl lipid containing GABA and the GABA-T inhibitor. gamma.-vinyl-GABA
Nishida et al.	1975	Female Sex Phermone of the German Cockroach, Blattella germanica (L.)(Orthoptera, Blattellidae), Responsible for Male Wing-Raising (I)
EP1469842A2 (de)	2004-10-27	Bicyclische cb2-cannabinoidrezeptor-liganden
BRPI0812919B1 (pt)	2019-01-29	composição farmacêutica que compreende um composto e kit
US6635672B1 (en)	2003-10-21	Agent for lowering prolactin
Tegtmeier et al.	1990	Eicosanoids in rat brain during ischemia and reperfusion—correlation to DC depolarization
US4725588A (en)	1988-02-16	Alkyl phospholipid antihypertensive agents in method of lowering blood pressure
CN113521038B (zh)	2025-08-01	一种麻醉药物组合物及其应用
Sloan et al.	1984	Acyloxyamines as prodrugs of anti-inflammatory carboxylic acids for improved delivery through skin
Juntunen et al.	2003	Anandamide prodrugs: 1. Water-soluble phosphate esters of arachidonylethanolamide and R-methanandamide
Rotman et al.	1975	Norepinephrine uptake sites in cardiac tissue. Lack of affinity of 6-hydroxynorepinephrine and related compounds
Haj-Yehia et al.	1992	Pharmacokinetic analysis of the structural requirements for forming “stable” analogues of valpromide
Fullerton et al.	1976	Cardenolide analogs. 1. A 17. beta.-unsaturated aldehyde
EP1507523A1 (de)	2005-02-23	Zimtsäure-dimere, ihre herstellung und verwendung zur behandlung von neurodegenerativen erkrankungen
Osgood et al.	1978	Drugs derived from cannabinoids. 7. Tachycardia and analgesia structure-activity relationships in. DELTA. 9-tetrahydrocannabinol and some synthetic analogs