CA2050623C - Ointments containing tricyclic compound - Google Patents
Ointments containing tricyclic compound Download PDFInfo
- Publication number
- CA2050623C CA2050623C CA002050623A CA2050623A CA2050623C CA 2050623 C CA2050623 C CA 2050623C CA 002050623 A CA002050623 A CA 002050623A CA 2050623 A CA2050623 A CA 2050623A CA 2050623 C CA2050623 C CA 2050623C
- Authority
- CA
- Canada
- Prior art keywords
- group
- ointment
- hydrogen atom
- compound
- hydroxy
- 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 - Lifetime
Links
- 239000002674 ointment Substances 0.000 title claims abstract description 66
- 150000001875 compounds Chemical class 0.000 title claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 28
- 230000003381 solubilizing effect Effects 0.000 claims abstract description 22
- 239000003883 ointment base Substances 0.000 claims abstract description 10
- -1 alkylene carbonate Chemical compound 0.000 claims description 60
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 22
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- CFZGEMKIQUVTCC-UHFFFAOYSA-N octacos-18-ene-2,3,10,16-tetrone Chemical compound CCCCCCCCCC=CCC(=O)CCCCCC(=O)CCCCCCC(=O)C(C)=O CFZGEMKIQUVTCC-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000013329 compounding Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 66
- 208000017520 skin disease Diseases 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 77
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 30
- 235000019271 petrolatum Nutrition 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000003871 white petrolatum Substances 0.000 description 22
- 229940057995 liquid paraffin Drugs 0.000 description 20
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 20
- 229940032159 propylene carbonate Drugs 0.000 description 20
- 239000007765 cera alba Substances 0.000 description 19
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 12
- 229940031578 diisopropyl adipate Drugs 0.000 description 12
- 239000012188 paraffin wax Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229940055577 oleyl alcohol Drugs 0.000 description 5
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000005103 alkyl silyl group Chemical group 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 239000004200 microcrystalline wax Substances 0.000 description 4
- 235000019808 microcrystalline wax Nutrition 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 3
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 229940074096 monoolein Drugs 0.000 description 3
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 2
- 229940117173 croton oil Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- OQQOAWVKVDAJOI-UHFFFAOYSA-N (2-dodecanoyloxy-3-hydroxypropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCC OQQOAWVKVDAJOI-UHFFFAOYSA-N 0.000 description 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- AFSHUZFNMVJNKX-LLWMBOQKSA-N 1,2-dioleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC\C=C/CCCCCCCC AFSHUZFNMVJNKX-LLWMBOQKSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
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- 208000023275 Autoimmune disease Diseases 0.000 description 1
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- 208000019300 CLIPPERS Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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- 208000035473 Communicable disease Diseases 0.000 description 1
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- 206010012442 Dermatitis contact Diseases 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
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- 201000004681 Psoriasis Diseases 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
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- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
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- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
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- 125000005907 alkyl ester group Chemical group 0.000 description 1
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- 231100000360 alopecia Toxicity 0.000 description 1
- 208000004631 alopecia areata Diseases 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- UHGPEWTZABDZCE-UHFFFAOYSA-N dipropyl decanedioate Chemical compound CCCOC(=O)CCCCCCCCC(=O)OCCC UHGPEWTZABDZCE-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229940095050 propylene Drugs 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 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
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229940117972 triolein Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP235177/1990 | 1990-09-04 | ||
| JP23517790 | 1990-09-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2050623A1 CA2050623A1 (en) | 1992-03-05 |
| CA2050623C true CA2050623C (en) | 2002-02-05 |
Family
ID=16982211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002050623A Expired - Lifetime CA2050623C (en) | 1990-09-04 | 1991-09-04 | Ointments containing tricyclic compound |
Country Status (20)
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5434094A (en) * | 1992-11-18 | 1994-06-08 | Fujisawa Pharmaceutical Co., Ltd. | Prolonged-action pharmaceutical preparation |
| JPH06345646A (ja) * | 1993-06-08 | 1994-12-20 | Fujisawa Pharmaceut Co Ltd | ローション剤 |
| AU735106B2 (en) * | 1994-10-26 | 2001-06-28 | Novartis Ag | Pharmaceutical compositions |
| DE69525957T2 (de) * | 1994-10-26 | 2002-11-14 | Novartis Ag | Verwendung eines ungesättigten Fettalkohols |
| DE19549794B4 (de) * | 1994-10-26 | 2009-07-30 | Novartis Ag | Pharmazeutische Zusammensetzungen |
| GB2327611B (en) * | 1994-10-26 | 1999-06-02 | Novartis Ag | Macrolide compositions |
| GB2327610B (en) * | 1994-11-04 | 1999-06-02 | Novartis Ag | Macrolide compositions |
| AR004480A1 (es) * | 1995-04-06 | 1998-12-16 | Amico Derin C D | Compuestos de ascomicina que poseen actividad antiinflamatoria, pro cedimiento para prepararlos, uso de dichos compuestos para preparar agentesfarmaceuticos y composiciones farmaceuticas que los incluyen |
| US5993787A (en) * | 1996-09-13 | 1999-11-30 | Johnson & Johnson Consumer Products, Inc. | Composition base for topical therapeutic and cosmetic preparations |
| WO1998029136A1 (en) * | 1996-12-27 | 1998-07-09 | Takeda Chemical Industries, Ltd. | Stabilized tricyclic compound |
| TW450810B (en) * | 1997-02-20 | 2001-08-21 | Fujisawa Pharmaceutical Co | Macrolides antibiotic pharmaceutical composition for preventing and treating skin diseases |
| GB9723669D0 (en) * | 1997-11-07 | 1998-01-07 | Univ Aberdeen | Skin penetration enhancing components |
| RU2149635C1 (ru) * | 1998-02-27 | 2000-05-27 | Пермская государственная медицинская академия | Способ лечения аллергических дерматитов |
| JP3732525B2 (ja) * | 1998-04-27 | 2006-01-05 | アステラス製薬株式会社 | 医薬組成物 |
| GB9817064D0 (en) * | 1998-08-05 | 1998-10-07 | Fujisawa Pharmaceutical Co | New use |
| US6307049B1 (en) | 1998-09-30 | 2001-10-23 | The Procter & Gamble Co. | Heterocyclic 2-substituted ketoamides |
| US6300341B1 (en) | 1998-09-30 | 2001-10-09 | The Procter & Gamble Co. | 2-substituted heterocyclic sulfonamides |
| GB9826656D0 (en) | 1998-12-03 | 1999-01-27 | Novartis Ag | Organic compounds |
| AUPR529701A0 (en) * | 2001-05-28 | 2001-06-21 | Fujisawa Pharmaceutical Co., Ltd. | Pharmaceutical composition |
| RU2183113C1 (ru) * | 2001-06-28 | 2002-06-10 | Новицкий Юрий Алексеевич | Средство-гидросульфат графита и способ лечения больных с доброкачественными и злокачественными опухолями кожи (варианты) |
| EP1406700A1 (en) * | 2001-07-06 | 2004-04-14 | Sucampo AG | Composition for topical administration comprising an interleukin-2 inhibitor and an antimicrobial agent |
| PE20030828A1 (es) * | 2002-03-04 | 2003-11-04 | Novartis Ag | Composicion oftalmica que comprende ascomicina |
| WO2004009056A1 (en) * | 2002-07-23 | 2004-01-29 | Novartis Ag | Ophtalmic ointment composition comprising a drug, an ointment base and a solubiling/dispersing agent |
| GB0218996D0 (en) * | 2002-08-14 | 2002-09-25 | Novartis Ag | Organic compounds |
| RU2231359C1 (ru) * | 2002-12-11 | 2004-06-27 | Государственное образовательное учреждение высшего профессионального образования Московская медицинская академия им. И.М.Сеченова | Способ лечения язвенных форм ангиитов кожи |
| US20090137556A1 (en) * | 2004-08-18 | 2009-05-28 | Ace Aps | Cosmetic and pharmaceutical compositions comprising ace inhibitors and/or angiotensin ii receptor antagonists |
| CA2526419C (en) * | 2005-01-04 | 2012-09-25 | Texas United Chemical Company, Llc | Compounded hydrocarbon oil and oil base drilling fluids prepared therefrom |
| CA2597537A1 (en) * | 2005-02-14 | 2006-08-17 | Akihiko Kamiya | Ointment |
| WO2006098353A1 (ja) * | 2005-03-15 | 2006-09-21 | Kyowa Hakko Kogyo Co., Ltd. | 外用剤 |
| CN104072534A (zh) * | 2005-10-05 | 2014-10-01 | 田边三菱制药株式会社 | 皮炎治疗剂 |
| AU2007218725B2 (en) | 2006-02-21 | 2011-12-01 | Eisai R & D Management Co., Ltd. | 4-(3-benzoylaminophenyl)-6,7-dimethoxy-2- methylaminoquinazoline derivative |
| EP2123641A4 (en) | 2007-02-16 | 2011-06-22 | Eisai R&D Man Co Ltd | CRYSTAL, AMORPHOUS FORM AND METHYL N-Ý3- (6,7-DIMETHOXY-2-METHYLAMINOQUINAZOLINE-4-YL) PHENYLENE TEREPHTALIC ACID SALT |
| US10265265B2 (en) | 2007-03-15 | 2019-04-23 | Drug Delivery Solutions Limited | Topical composition |
| CA2696793A1 (en) | 2007-08-17 | 2009-02-26 | Eisai R&D Management Co., Ltd. | Novel preparation for external use |
| CN102532041A (zh) | 2007-08-17 | 2012-07-04 | 卫材R&D管理有限公司 | 喹唑啉衍生物的制造方法 |
| EP2345414B1 (en) * | 2008-10-08 | 2014-06-25 | Takata Seiyaku Co., Ltd. | Tacrolimus preparation for external applications |
| JP2010132607A (ja) * | 2008-12-05 | 2010-06-17 | Taisho Pharm Ind Ltd | アトピー性皮膚炎治療用軟膏剤 |
| JP2010202546A (ja) * | 2009-03-02 | 2010-09-16 | Taisho Pharm Ind Ltd | アトピー性皮膚炎の治療用軟膏製剤 |
| AU2012211809A1 (en) * | 2011-01-31 | 2013-09-05 | Osaka University | Externally-used drug for treating skin disorder and method for producing same |
| CN102885761B (zh) * | 2012-09-24 | 2015-08-05 | 浙江万晟药业有限公司 | 一种制备他克莫司软膏的方法 |
| RU2538680C2 (ru) * | 2013-03-12 | 2015-01-10 | Открытое акционерное общество "Химико-фармацевтический комбинат "АКРИХИН" (ОАО "АКРИХИН") | Фармацевтическая композиция для лечения атопического дерматита и способ ее получения |
| RU2553600C2 (ru) * | 2013-05-16 | 2015-06-20 | Открытое акционерное общество "Химико-фармацевтический комбинат "АКРИХИН" (ОАО "АКРИХИН") | Фармацевтическая композиция для лечения заболеваний кожи |
| CN104127369A (zh) * | 2014-07-02 | 2014-11-05 | 人福医药集团股份公司 | 他克莫司软膏及其制备方法 |
| US10143682B2 (en) | 2014-10-28 | 2018-12-04 | Koushi Yamaguchi | Medicine for improving state of pregnancy, and use thereof |
| CN106309353A (zh) * | 2015-06-19 | 2017-01-11 | 江苏吉贝尔药业股份有限公司 | 一种治疗银屑病的软膏剂及其制备方法 |
| RU2741504C2 (ru) | 2016-04-04 | 2021-01-26 | Драг Деливери Солюшнз Лимитед | Композиция для местного применения, включающая такролимус |
| CN105769752B (zh) * | 2016-04-08 | 2018-12-11 | 湖北人福成田药业有限公司 | 制备他克莫司软膏的方法及他克莫司软膏 |
| EP3542788A1 (en) | 2018-03-19 | 2019-09-25 | MC2 Therapeutics Limited | Topical composition comprising calcipotriol and betamethasone dipropionate |
| JP7465806B2 (ja) | 2018-08-10 | 2024-04-11 | 晃史 山口 | 母体と胎児との関係における液性免疫関連疾患の治療薬 |
| EP3930713B1 (en) | 2018-12-04 | 2025-05-28 | Ilko Ilaç Sanayi Ve Ticaret Anonim Sirketi | Stable tacrolimus ointment formulation for topical treatment of skin conditions |
| AU2019401108A1 (en) | 2018-12-18 | 2021-07-01 | Koushi Yamaguchi | Agent for improving infertility, recurrent miscarriage, and state of pregnancy |
| CN112439071B (zh) * | 2019-09-04 | 2022-05-20 | 武汉科福新药有限责任公司 | 透皮促渗组合物及其在噻吗洛尔制剂中的应用 |
| CN116056687A (zh) * | 2020-03-02 | 2023-05-02 | 上海奥科达医药科技股份有限公司 | 含有mtor抑制剂的外用制剂 |
| CN112022798B (zh) * | 2020-08-11 | 2022-04-29 | 四川大学华西医院 | 一种速效他克莫司软膏、制备方法及应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK175235B1 (da) * | 1987-11-09 | 2004-07-19 | Novartis Ag | Ny anvendelse af azatricycloderivater og farmaceutiske præparater med indhold deraf |
| KR0159766B1 (ko) * | 1989-10-16 | 1998-12-01 | 후지사와 토모키치로 | 양모제 조성물 |
| US5061700A (en) * | 1989-11-16 | 1991-10-29 | Gordon Jay Dow | Glyceryl acetate ointment vehicles |
-
1991
- 1991-08-30 AT AT91114598T patent/ATE150304T1/de not_active IP Right Cessation
- 1991-08-30 ES ES91114598T patent/ES2099112T3/es not_active Expired - Lifetime
- 1991-08-30 AU AU83515/91A patent/AU656145B2/en not_active Expired
- 1991-08-30 DE DE69125230T patent/DE69125230T2/de not_active Expired - Lifetime
- 1991-08-30 EP EP91114598A patent/EP0474126B1/en not_active Expired - Lifetime
- 1991-08-30 DK DK91114598.5T patent/DK0474126T3/da active
- 1991-08-30 SG SG1996005797A patent/SG46547A1/en unknown
- 1991-09-02 IE IE308591A patent/IE913085A1/en not_active IP Right Cessation
- 1991-09-02 KR KR1019910015225A patent/KR100194240B1/ko not_active Expired - Lifetime
- 1991-09-03 PH PH43041A patent/PH31282A/en unknown
- 1991-09-03 ZA ZA916983A patent/ZA916983B/xx unknown
- 1991-09-03 RU SU5001707/14A patent/RU2079303C1/ru active Protection Beyond IP Right Term
- 1991-09-03 HU HU912846A patent/HUT59002A/hu unknown
- 1991-09-04 CA CA002050623A patent/CA2050623C/en not_active Expired - Lifetime
- 1991-09-04 CN CN91108796A patent/CN1069193C/zh not_active Expired - Lifetime
- 1991-09-04 PT PT98862A patent/PT98862B/pt not_active IP Right Cessation
- 1991-09-04 JP JP3224418A patent/JP2526752B2/ja not_active Expired - Lifetime
-
1993
- 1993-05-17 US US08/062,330 patent/US5385907A/en not_active Expired - Lifetime
-
1995
- 1995-06-22 HU HU95P/P00363P patent/HU211470A9/hu unknown
-
1997
- 1997-03-21 GR GR970400563T patent/GR3022883T3/el unknown
- 1997-07-10 HK HK97101531A patent/HK1000006A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0474126B1 (en) | 1997-03-19 |
| AU656145B2 (en) | 1995-01-27 |
| DK0474126T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1997-04-07 |
| PH31282A (en) | 1998-07-06 |
| CN1059468A (zh) | 1992-03-18 |
| HUT59002A (en) | 1992-04-28 |
| KR100194240B1 (ko) | 1999-06-15 |
| DE69125230T2 (de) | 1997-07-10 |
| PT98862B (pt) | 1999-02-26 |
| AU8351591A (en) | 1992-03-12 |
| JP2526752B2 (ja) | 1996-08-21 |
| JPH0517481A (ja) | 1993-01-26 |
| ZA916983B (en) | 1992-05-27 |
| DE69125230D1 (de) | 1997-04-24 |
| GR3022883T3 (en) | 1997-06-30 |
| HU211470A9 (en) | 1995-11-28 |
| CA2050623A1 (en) | 1992-03-05 |
| ATE150304T1 (de) | 1997-04-15 |
| US5385907A (en) | 1995-01-31 |
| CN1069193C (zh) | 2001-08-08 |
| ES2099112T3 (es) | 1997-05-16 |
| RU2079303C1 (ru) | 1997-05-20 |
| HK1000006A1 (en) | 1997-10-03 |
| KR920005987A (ko) | 1992-04-27 |
| EP0474126A1 (en) | 1992-03-11 |
| PT98862A (pt) | 1992-08-31 |
| SG46547A1 (en) | 1998-02-20 |
| IE913085A1 (en) | 1992-03-11 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKEX | Expiry |