WO1996018600B1 - Amides d'acides mono et bicarboxyliques a amino amines, ou glycosamines, a activite selective sur le recepteur peripherique des cannabinoides - Google Patents
Amides d'acides mono et bicarboxyliques a amino amines, ou glycosamines, a activite selective sur le recepteur peripherique des cannabinoidesInfo
- Publication number
- WO1996018600B1 WO1996018600B1 PCT/EP1995/004926 EP9504926W WO9618600B1 WO 1996018600 B1 WO1996018600 B1 WO 1996018600B1 EP 9504926 W EP9504926 W EP 9504926W WO 9618600 B1 WO9618600 B1 WO 9618600B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- group
- groups
- pathologies
- linear
- Prior art date
Links
- 150000002337 glycosamines Chemical class 0.000 title claims abstract 8
- 150000001413 amino acids Chemical class 0.000 title claims abstract 5
- 150000001408 amides Chemical class 0.000 title claims 21
- 239000002253 acid Substances 0.000 title claims 6
- 230000002093 peripheral effect Effects 0.000 title claims 3
- 150000007513 acids Chemical class 0.000 title claims 2
- 229930003827 cannabinoid Natural products 0.000 title claims 2
- 239000003557 cannabinoid Substances 0.000 title claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract 9
- 229930195733 hydrocarbon Natural products 0.000 claims abstract 9
- 235000001014 amino acid Nutrition 0.000 claims abstract 4
- -1 beta-Alamine Natural products 0.000 claims abstract 2
- 230000007170 pathology Effects 0.000 claims 25
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 238000000034 method Methods 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 4
- 230000001684 chronic effect Effects 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- 230000004075 alteration Effects 0.000 claims 3
- BPUGEZYWFKORPB-BYEBANRISA-N 3-hydroxy-n-[(2s,3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]tetradecanamide Chemical compound CCCCCCCCCCCC(O)CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O BPUGEZYWFKORPB-BYEBANRISA-N 0.000 claims 2
- 201000009906 Meningitis Diseases 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 230000009089 cytolysis Effects 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 2
- 239000000499 gel Substances 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000002674 ointment Substances 0.000 claims 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 claims 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims 1
- MSWZFWKMSRAUBD-CBPJZXOFSA-N 2-amino-2-deoxy-D-mannopyranose Chemical compound N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-CBPJZXOFSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims 1
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims 1
- 241000459479 Capsula Species 0.000 claims 1
- 241000701022 Cytomegalovirus Species 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- 206010027202 Meningitis bacterial Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010028813 Nausea Diseases 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 235000021319 Palmitoleic acid Nutrition 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 208000005392 Spasm Diseases 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 1
- 235000008206 alpha-amino acids Nutrition 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 201000009904 bacterial meningitis Diseases 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 claims 1
- 239000003124 biologic agent Substances 0.000 claims 1
- 230000001612 cachectic effect Effects 0.000 claims 1
- 229940065144 cannabinoids Drugs 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003492 excitotoxic effect Effects 0.000 claims 1
- 231100000063 excitotoxicity Toxicity 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 229940102223 injectable solution Drugs 0.000 claims 1
- 229940102213 injectable suspension Drugs 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000004005 microsphere Substances 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- 230000008693 nausea Effects 0.000 claims 1
- 230000000626 neurodegenerative effect Effects 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 235000021313 oleic acid Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000011505 plaster Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000020341 sensory perception of pain Effects 0.000 claims 1
- 210000000278 spinal cord Anatomy 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- MAZWDMBCPDUFDJ-UHFFFAOYSA-N trans-Traumatinsaeure Natural products OC(=O)CCCCCCCCC=CC(O)=O MAZWDMBCPDUFDJ-UHFFFAOYSA-N 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- MAZWDMBCPDUFDJ-VQHVLOKHSA-N traumatic acid Chemical compound OC(=O)CCCCCCCC\C=C\C(O)=O MAZWDMBCPDUFDJ-VQHVLOKHSA-N 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 abstract 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 1
- 150000001944 cysteine derivatives Chemical class 0.000 abstract 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 abstract 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000003354 serine derivatives Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Abstract
Le très grand nombre de composés théoriquement concevables résultant de la combinaison de tous les substituants revendiqués dans la formule (I) empêche une recherche complète. Pour des raisons économiques, on a limité la recherche aux composés suivants: R1 représente un radical hydrocarbure qui n'est pas substitué ou l'est par seulement un groupe OH et possède une chaîne linéaire d'au moins 8 atomes de carbone (A), le groupe NR2R3 représente soit un acide aminé alpha, bêta ou gamma (par exemple des acides aminés comme la proline ne sont pas compris), ou un reste glycosamine. Malgré la limitation ci-dessus mentionnée, la recherche a donné un trop grand nombre de composés pertinents. En conséquence, on a encore limité celle-ci à des composés dans lesquels NR2R3 représente glycine, bêta-alanine, l'acide gamma-amino-butyrique, des dérivés sérine ou cystéine, ou glycosamine possédant les structures suivantes: (a), (b), (c). On a relevé un nombre encore trop grand de composés pertinents que l'on ne peut pas tous citer dans le rapport de cette recherche. Les documents cités constituent seulement une sélection arbitraire et le rapport de la recherche doit être considéré comme incomplet. On décrit des amides d'acides mono et bicarboxyliques à acides aminés ou glycosamines, à activité sélective sur le récepteur périphérique des cannabinoïdes, ainsi que l'utilisation de ces amides dans le traitement de pathologies associées à la modulation dudit récepteur. On décrit également le procédé de préparation de ces amides ainsi que des compositions pharmaceutiques les contenant.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002207804A CA2207804C (fr) | 1994-12-14 | 1995-12-13 | Amides d'acides mono et bicarboxyliques a amino amines, ou glycosamines, a activite selective sur le recepteur peripherique des cannabinoides |
| AU43441/96A AU4344196A (en) | 1994-12-14 | 1995-12-13 | Amides of mono and bicarboxylic acids with amino acids or glycosamines, selectively active on the cannabinoid peripheral receptor |
| JP51826496A JP4111349B2 (ja) | 1994-12-14 | 1995-12-13 | カンナビノイド末梢レセプターに選択的に作用するモノおよびビカルボン酸のアミノ酸あるいはグリコサミンとのアミド類 |
| EP95942141A EP0799188B1 (fr) | 1994-12-14 | 1995-12-13 | Amides d'acides mono et bicarboxyliques a glycosamines, a activite selective sur le recepteur peripherique des cannabinoides |
| DE69512273T DE69512273T2 (de) | 1994-12-14 | 1995-12-13 | Amide von mono-und dicarbonsäuren mit glycosaminen, mit selektiver wirkung auf den peripheren cannabinoiden rezeptor |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI942513A IT1271267B (it) | 1994-12-14 | 1994-12-14 | Ammidi di acidi mono e bicarbossilici con amminoalcoli,selettivamente attive sul recettore periferico dei cannabinoidi |
| ITMI94A002513 | 1994-12-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996018600A1 WO1996018600A1 (fr) | 1996-06-20 |
| WO1996018600B1 true WO1996018600B1 (fr) | 1996-08-29 |
Family
ID=11369990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1995/004926 WO1996018600A1 (fr) | 1994-12-14 | 1995-12-13 | Amides d'acides mono et bicarboxyliques a amino amines, ou glycosamines, a activite selective sur le recepteur peripherique des cannabinoides |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0799188B1 (fr) |
| JP (1) | JP4111349B2 (fr) |
| AT (1) | ATE184591T1 (fr) |
| AU (1) | AU4344196A (fr) |
| CA (1) | CA2207804C (fr) |
| DE (1) | DE69512273T2 (fr) |
| IL (1) | IL116401A0 (fr) |
| IT (1) | IT1271267B (fr) |
| WO (1) | WO1996018600A1 (fr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19706903A1 (de) | 1997-02-21 | 1998-08-27 | Bayer Ag | Verwendung von bekannten Agonisten des zentralen Cannabinoid-Rezeptors CB 1 |
| JP2002512188A (ja) | 1998-04-21 | 2002-04-23 | ザ ガバメント オブ ザ ユナイテッド ステイツ オブ アメリカ， アズ レプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ | 抗酸化剤及び神経保護剤としてのカンナビノイド類 |
| WO2000066260A1 (fr) * | 1999-04-28 | 2000-11-09 | Toray Industries, Inc. | Matieres servant a eliminer des cannabinoides et colonnes utiles pour eliminer des cannabinoides a l'aide de ces matieres |
| US6864285B1 (en) | 1999-07-07 | 2005-03-08 | Innovet Italia S.R.L. | Covalent derivatives of alkanolamides of monocarboxylic and dicarboxylic acids functionally active on the CB2 cannabinoid receptor |
| EP1361872A4 (fr) * | 2000-10-03 | 2004-05-19 | Univ Virginia | Nouveaux agonistes et antagonistes des recepteurs de l'acide lysophosphatidique |
| US8449908B2 (en) | 2000-12-22 | 2013-05-28 | Alltranz, Llc | Transdermal delivery of cannabidiol |
| ATE446303T1 (de) | 2001-01-30 | 2009-11-15 | Univ Virginia | Agonisten und antagonisten von sphingosin-1- phosphatrezeptoren |
| ITMI20011483A1 (it) * | 2001-07-11 | 2003-01-11 | Res & Innovation Soc Coop A R | Uso di composti come antagonisti funzionali ai recettori centrali deicannabinoidi |
| EP2130820A1 (fr) | 2002-02-19 | 2009-12-09 | Shionogi & Co., Ltd. | Antiprurigineux |
| EP1487436A4 (fr) | 2002-03-08 | 2009-06-03 | Signal Pharm Inc | Polytherapie destinee a traiter, prevenir ou gerer des troubles proliferatifs et des cancers |
| ES2284807T3 (es) * | 2002-06-26 | 2007-11-16 | Innovet Italia S.R.L. | Composicion farmaceutica para prevenir el desarrollo y la progresion de enfermedades cutaneas superficiales. |
| EP1543821B1 (fr) | 2002-07-25 | 2008-02-13 | Lion Corporation | Preparations externes |
| WO2004082673A1 (fr) * | 2003-03-20 | 2004-09-30 | Menicon Co. Ltd. | Composition ophtalmique liquide |
| WO2005115150A2 (fr) | 2004-05-06 | 2005-12-08 | University Of Virginia Patent Foundation | Nouveaux antagonistes selectifs du recepteur de l'acide lysophosphatidique |
| ITMI20041567A1 (it) * | 2004-07-30 | 2004-10-30 | Maycos Italiana Di Comini Miro | "derivati n-acilati di acidi bicarbossilici con amminoacidi e con idrolizzati proteici vegetali e loro applicazione in prodotti cosmetici, dermofarmaceutici e farmaceutici" |
| JP2010535238A (ja) | 2007-07-30 | 2010-11-18 | オールトランツ インコーポレイティド | カンナビジオールのプロドラッグ、カンナビジオールのプロドラッグを含む組成物及びその使用方法 |
| US8198327B2 (en) | 2008-04-09 | 2012-06-12 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Fatty acid amides and uses thereof |
| MY144409A (en) * | 2009-04-09 | 2011-09-15 | Malaysian Palm Oil Board | A method of producing derivatives of azelaic acid |
| EP2667843A2 (fr) * | 2011-01-24 | 2013-12-04 | Yissum Research Development Company of the Hebrew University of Jerusalem, Ltd. | Nanoparticules à base d'acide poly(lactique glycolique) pour applications cosmétiques |
| KR20160147960A (ko) | 2014-04-25 | 2016-12-23 | 아지노모토 가부시키가이샤 | 면역자극제 |
| EP3511318A1 (fr) | 2015-10-28 | 2019-07-17 | Ajinomoto Co., Inc. | Agent immunostimulant |
| IT201800000728A1 (it) * | 2018-01-11 | 2019-07-11 | Univ Degli Studi Di Milano Bicocca | Nuovi antagonisti del tlr4 umano |
| IT201800003912A1 (it) * | 2018-03-26 | 2019-09-26 | Innovet Italia Srl | N-palmitoil-d-glucosamina in forma micronizzata |
| EP3574899A1 (fr) * | 2018-05-28 | 2019-12-04 | Université de Bourgogne | Dérivés d'acide oléique, composition pharmaceutique ou composition alimentaire comprenant lesdits dérivés d'acide oléique et leurs utilisations |
| CN112341354B (zh) * | 2020-09-24 | 2022-06-10 | 湖北泓肽生物科技有限公司 | 一种pms的合成方法 |
| CN113502153B (zh) * | 2021-07-07 | 2023-02-14 | 哈尔滨工程大学 | 一种非芳香性发光小分子/SiO2杂化的荧光纳米材料及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5117535B2 (fr) * | 1973-04-23 | 1976-06-03 | ||
| JPS5117534B2 (fr) * | 1973-04-23 | 1976-06-03 | ||
| JPS5850961B2 (ja) * | 1976-11-05 | 1983-11-14 | カネボウ株式会社 | 安定化された毛髪染色用組成物 |
| US4933363A (en) * | 1988-08-16 | 1990-06-12 | Elsohly Mahmoud A | Method for effecting systemic delivery of delta-9-tetrahydrocannabinol |
| US4999417A (en) * | 1989-03-30 | 1991-03-12 | Nova Pharmaceutical Corporation | Biodegradable polymer compositions |
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| IL101708A (en) * | 1992-04-28 | 1996-08-04 | Senyorina Ltd | Anti-fattening drugs comprising amino acid derivatives |
| JP3435195B2 (ja) * | 1992-10-30 | 2003-08-11 | 花王株式会社 | 皮脂分泌抑制剤 |
| IL103932A (en) * | 1992-11-30 | 1997-02-18 | Yissum Res & Dev | Fatty acid and pharmaceutical compositions containing them |
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1994
- 1994-12-14 IT ITMI942513A patent/IT1271267B/it active IP Right Grant
-
1995
- 1995-12-13 DE DE69512273T patent/DE69512273T2/de not_active Expired - Lifetime
- 1995-12-13 AT AT95942141T patent/ATE184591T1/de active
- 1995-12-13 WO PCT/EP1995/004926 patent/WO1996018600A1/fr active IP Right Grant
- 1995-12-13 EP EP95942141A patent/EP0799188B1/fr not_active Expired - Lifetime
- 1995-12-13 AU AU43441/96A patent/AU4344196A/en not_active Abandoned
- 1995-12-13 CA CA002207804A patent/CA2207804C/fr not_active Expired - Lifetime
- 1995-12-13 JP JP51826496A patent/JP4111349B2/ja not_active Expired - Lifetime
- 1995-12-14 IL IL11640195A patent/IL116401A0/xx unknown
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