JPH0643390B2 - アザシクロアルカン誘導体 - Google Patents
アザシクロアルカン誘導体Info
- Publication number
- JPH0643390B2 JPH0643390B2 JP61079174A JP7917486A JPH0643390B2 JP H0643390 B2 JPH0643390 B2 JP H0643390B2 JP 61079174 A JP61079174 A JP 61079174A JP 7917486 A JP7917486 A JP 7917486A JP H0643390 B2 JPH0643390 B2 JP H0643390B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- drug
- present
- hours
- group
- 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
- 150000003976 azacycloalkanes Chemical class 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 59
- 239000003814 drug Substances 0.000 description 29
- 239000000203 mixture Substances 0.000 description 29
- 229940079593 drug Drugs 0.000 description 28
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- -1 2-propylthioethyl Chemical group 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- 229960002508 pindolol Drugs 0.000 description 13
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
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- 238000009472 formulation Methods 0.000 description 12
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 11
- 239000008280 blood Substances 0.000 description 10
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
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- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 6
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- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 5
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- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
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- 229960004580 glibenclamide Drugs 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
- 239000004365 Protease Substances 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
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- 239000008187 granular material Substances 0.000 description 3
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- 229920000609 methyl cellulose Polymers 0.000 description 3
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- 235000010981 methylcellulose Nutrition 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
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- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 208000019300 CLIPPERS Diseases 0.000 description 2
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 108010026389 Gramicidin Proteins 0.000 description 2
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- 229910002651 NO3 Inorganic materials 0.000 description 2
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 2
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- 235000019482 Palm oil Nutrition 0.000 description 2
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 2
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- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- UGGAILYEBCSZIV-ITJSPEIASA-N Siccanin Chemical compound C1CCC(C)(C)[C@@H]2CC[C@]3(C)OC4=CC(C)=CC(O)=C4[C@H]4[C@@H]3[C@@]21CO4 UGGAILYEBCSZIV-ITJSPEIASA-N 0.000 description 2
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- 229940083542 sodium Drugs 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- LARLNXOUTTUXPN-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonyl-(5-methyl-1,2-oxazol-3-yl)azanide Chemical compound [Na+].O1C(C)=CC([N-]S(=O)(=O)C=2C=CC(N)=CC=2)=N1 LARLNXOUTTUXPN-UHFFFAOYSA-N 0.000 description 1
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
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- 229960005202 streptokinase Drugs 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
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- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
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- BJYLYJCXYAMOFT-RSFVBTMBSA-N tacalcitol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CC[C@@H](O)C(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C BJYLYJCXYAMOFT-RSFVBTMBSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229960000874 thyrotropin Drugs 0.000 description 1
- 230000001748 thyrotropin Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960000363 trapidil Drugs 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- 229960001177 trimetazidine Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940045136 urea Drugs 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229950009268 zinostatin Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/06—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (21)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61079174A JPH0643390B2 (ja) | 1986-04-08 | 1986-04-08 | アザシクロアルカン誘導体 |
EP87200183A EP0241050B1 (en) | 1986-04-08 | 1987-02-07 | Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparation containing the absorption promoters |
ES198787200183T ES2046196T3 (es) | 1986-04-08 | 1987-02-07 | Derivados de azacicloalcanos, promotores de absorcion que contienen los derivados como ingrediente eficaz y preparaciones externas que contienen los promotores de absorcion. |
DE8787200183T DE3782182T2 (de) | 1986-04-08 | 1987-02-07 | Azacycloalkanderivate, absorptionspromotoren, die die derivate als effektiven inhaltsstoff enthalten und aeusserlich anzuwendende praeparate, die absorptionspromotoren enthalten. |
AT87200183T ATE81505T1 (de) | 1986-04-08 | 1987-02-07 | Azacycloalkanderivate, absorptionspromotoren, die die derivate als effektiven inhaltsstoff enthalten und aeusserlich anzuwendende praeparate, die absorptionspromotoren enthalten. |
KR1019900702502A KR910000480B1 (ko) | 1986-04-08 | 1987-02-10 | 아자시클로 알칸유도체의 제조방법 |
KR1019870701153A KR910000164B1 (ko) | 1986-04-08 | 1987-02-10 | 아자시클로알칸유도체의 제조방법 |
CA000529377A CA1336597C (en) | 1986-04-08 | 1987-02-10 | Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparations containing the absorption promoters |
AU70207/87A AU601402B2 (en) | 1986-04-08 | 1987-02-10 | Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparations containing the absorption promoters |
KR1019900702501A KR910000479B1 (ko) | 1986-04-08 | 1987-02-10 | 아자시클로알칸유도체의 제조방법 |
PCT/JP1987/000086 WO1987006226A2 (en) | 1986-04-08 | 1987-02-10 | Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparations containing the absorption promoters |
AR87306713A AR245107A1 (es) | 1986-04-08 | 1987-02-11 | Procedimiento para preparar derivados de azacicloalcano,promotores de absorcion que contienen a los derivados como el ingrediente eficaz y preparaciones externas que contienen a los promotores |
CN87100666A CN1018452B (zh) | 1986-04-08 | 1987-02-12 | 制备氮杂环烷烃衍生物的方法 |
CN91109720A CN1020605C (zh) | 1986-04-08 | 1987-02-12 | 制备氮杂环烷烃衍生物的方法 |
US07/131,193 US4882359A (en) | 1986-04-08 | 1987-11-18 | Azacycloalkane derivatives, absorption promoters containing the derivatives as the effective ingredient and external preparations containing the absorption promoters |
SU874203780A SU1748644A3 (ru) | 1986-04-08 | 1987-12-07 | Способ получени производных азациклоалкана |
SU894613462A SU1750422A3 (ru) | 1986-04-08 | 1989-02-13 | Способ получени лактамов |
SU894613514A SU1750423A3 (ru) | 1986-04-08 | 1989-02-27 | Способ получени лактамов |
KR9072500A KR910000478B1 (en) | 1986-04-08 | 1990-11-22 | Process for preparing azacycloalkane derivatives |
CN 91109721 CN1019573B (zh) | 1986-04-08 | 1991-10-16 | 制备氮杂环烷烃衍生物的方法 |
GR930400029T GR3006768T3 (en]) | 1986-04-08 | 1993-01-13 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61079174A JPH0643390B2 (ja) | 1986-04-08 | 1986-04-08 | アザシクロアルカン誘導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62238261A JPS62238261A (ja) | 1987-10-19 |
JPH0643390B2 true JPH0643390B2 (ja) | 1994-06-08 |
Family
ID=13682615
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61079174A Expired - Lifetime JPH0643390B2 (ja) | 1986-04-08 | 1986-04-08 | アザシクロアルカン誘導体 |
Country Status (14)
Country | Link |
---|---|
US (1) | US4882359A (en]) |
EP (1) | EP0241050B1 (en]) |
JP (1) | JPH0643390B2 (en]) |
KR (1) | KR910000164B1 (en]) |
CN (2) | CN1020605C (en]) |
AR (1) | AR245107A1 (en]) |
AT (1) | ATE81505T1 (en]) |
AU (1) | AU601402B2 (en]) |
CA (1) | CA1336597C (en]) |
DE (1) | DE3782182T2 (en]) |
ES (1) | ES2046196T3 (en]) |
GR (1) | GR3006768T3 (en]) |
SU (3) | SU1748644A3 (en]) |
WO (1) | WO1987006226A2 (en]) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3779833T2 (de) * | 1986-01-31 | 1993-02-04 | Whitby Research Inc | Zusammensetzungen enthaltend 1-substituierte azacycloalkane und deren verwendung. |
US5472946A (en) * | 1988-04-08 | 1995-12-05 | Peck; James V. | Transdermal penetration enhancers |
CA1334646C (en) * | 1988-04-08 | 1995-03-07 | James Vanolden Peck | Transdermal penetration enhancers |
US5234959A (en) * | 1988-04-08 | 1993-08-10 | Whitby Research, Inc. | Penetration enhancers for transdermal delivery of systemic agents |
US5041435A (en) * | 1988-08-13 | 1991-08-20 | Santen Pharmaceutical Co., Ltd. | Cyclic sulfur-containing compounds |
ES2063369T3 (es) * | 1989-08-03 | 1995-01-01 | Hisamitsu Pharmaceutical Co | Crema para la piel, para uso externo. |
IL91928A (en) * | 1989-10-08 | 1994-07-31 | Amrad Res & Dev | Pharmaceutical compositions containing prolactin |
US5070084A (en) * | 1990-02-26 | 1991-12-03 | Campbell James N | Treatment of sympathetically maintained pain |
US6559186B1 (en) | 1990-02-26 | 2003-05-06 | Arc 1, Inc. | Compositions and methods of treatment of sympathetically maintained pain |
FR2663932B1 (fr) * | 1990-06-29 | 1994-04-29 | Cird Galderma | N-alkyl oxo-1 et dioxo-1,1 thiamorpholinones-3 et leurs utilisations comme agents de penetration de composes actifs dans des compositions therapeutiques et cosmetiques. |
JPH078806B2 (ja) * | 1990-08-16 | 1995-02-01 | 旭化成工業株式会社 | カルシトニン類含有経鼻投与用乳剤 |
FR2666962B1 (fr) * | 1990-09-26 | 1996-06-14 | Oreal | Composition antifongique sous forme de spray sec. |
US5158763A (en) * | 1990-10-09 | 1992-10-27 | Colgate-Palmolive Company | Non-staining anti-bacterial oral composition |
JPH07595B2 (ja) * | 1990-10-31 | 1995-01-11 | 久光製薬株式会社 | アザシクロアルカン誘導体の製造方法 |
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JP3090353B2 (ja) * | 1991-09-17 | 2000-09-18 | 旭化成工業株式会社 | パラチロイドホルモン類含有経鼻投与用乳剤 |
EP0608433B1 (en) * | 1992-07-13 | 2004-05-19 | Shiseido Company, Ltd. | Composition for dermatologic preparation |
WO1995011042A1 (fr) * | 1993-10-21 | 1995-04-27 | Hisamitsu Pharmaceutical Co., Inc. | Composition administree par voie nasale et preparation contenant celle-ci |
DE4337945A1 (de) * | 1993-11-06 | 1995-05-11 | Labtec Gmbh | Pflaster zur Behandlung von Nagelmykosen |
GB9325854D0 (en) * | 1993-12-17 | 1994-02-23 | Smithkline Beecham Corp | Porcess |
US6262117B1 (en) | 1999-02-18 | 2001-07-17 | Allergan Sales, Inc. | Method and composition for treating acne |
JP2000247911A (ja) | 1999-02-26 | 2000-09-12 | Hisamitsu Pharmaceut Co Inc | 大腸用吸収促進剤 |
JP4653282B2 (ja) * | 2000-05-23 | 2011-03-16 | 昭和薬品化工株式会社 | ミノサイクリン含有組成物 |
RU2311409C2 (ru) * | 2003-01-10 | 2007-11-27 | Ф.Хоффманн-Ля Рош Аг | Производные 2-пиперидона в качестве агонистов простагландина |
JP4504210B2 (ja) * | 2005-01-25 | 2010-07-14 | 花王株式会社 | 染毛剤組成物 |
US8026266B2 (en) | 2005-11-08 | 2011-09-27 | Arcion Therapeutics, Inc. | Treatment of length dependent neuropathy |
CN118141709B (zh) * | 2024-02-22 | 2025-04-22 | 北京逆之龄生物科技有限公司 | 一种抗衰老化妆品及其制备方法和应用 |
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US4450102A (en) | 1982-11-02 | 1984-05-22 | Phillips Petroleum Company | Sulfur based metal cleaners and corrosion inhibitors |
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DE871154C (de) * | 1942-08-26 | 1953-03-19 | Basf Ag | Verfahren zur Herstellung oberflaechenwirksamer Verbindungen |
GB947910A (en) * | 1960-11-04 | 1964-01-29 | Gen Aniline & Film Corp | Surface active ethers of n-(hydroxymethyl)-lactams |
US3188317A (en) * | 1961-12-22 | 1965-06-08 | Dow Chemical Co | Oxazolidinone derivatives |
US3228955A (en) * | 1962-01-18 | 1966-01-11 | Dow Chemical Co | Certain substituted oxazolidinones and pyrrolidinones |
DE1177641B (de) * | 1962-06-12 | 1964-09-10 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von N-(ª‰-Hydroxy-alkyl)-oxazolidonen-(4) bzw. deren Polyaether |
DE1241830B (de) * | 1962-11-02 | 1967-06-08 | Kalk Chemische Fabrik Gmbh | Verfahren zur Herstellung von AEthern des N-Methylol-2, 2, 5, 5-tetramethyloxazolidons-(4) |
US3232952A (en) * | 1963-09-20 | 1966-02-01 | Kalk Chemische Fabrik Gmbh | Di-(oxazolidinone-(4)-n-alkyl)-ethers |
DE1695846A1 (de) * | 1967-05-05 | 1971-05-13 | Schwarzkopf Gmbh Hans | Verfahren zur Darstellung von Thioaethern mit reduktiven Eigenschaften |
DE2114295A1 (de) * | 1970-03-27 | 1971-10-14 | Gaf Corp | Substituierte AEtherderivate des N-Hydroxymethyl-2-pyrrolidinon und Verfahren zu deren Herstellung |
DE2114251A1 (de) * | 1970-03-30 | 1971-10-14 | Gaf Corp | Tertiaere Aminomethylderivate des N-Hydroxymethyl-2-pyrrolidinon und Verfahren zu deren Herstellung |
US3956313A (en) * | 1970-04-13 | 1976-05-11 | Gaf Corporation | N-(substituted-thiomethyl)-2-pyrrolidinones |
US3991203A (en) * | 1975-06-19 | 1976-11-09 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacyclopentan-2-ones |
US4415563A (en) * | 1980-04-04 | 1983-11-15 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacyclononan-2-ones |
US4424210A (en) * | 1980-04-04 | 1984-01-03 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloalkan-2-ones |
US4444762A (en) * | 1980-04-04 | 1984-04-24 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacyclopentan-2-ones |
US4423040A (en) * | 1980-04-04 | 1983-12-27 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacyclohexan-2-ones |
FR2525106B1 (fr) * | 1982-04-15 | 1985-06-07 | Oreal | Composition cosmetique contenant en tant qu'agent actif sur l'elasticite et la souplesse de la peau, de la thiamorpholinone ou l'un de ses derives |
FR2525220A1 (fr) * | 1982-04-15 | 1983-10-21 | Oreal | Nouveaux derives substitues de la thiamorpholinone et leurs procedes de preparation |
-
1986
- 1986-04-08 JP JP61079174A patent/JPH0643390B2/ja not_active Expired - Lifetime
-
1987
- 1987-02-07 EP EP87200183A patent/EP0241050B1/en not_active Expired - Lifetime
- 1987-02-07 ES ES198787200183T patent/ES2046196T3/es not_active Expired - Lifetime
- 1987-02-07 AT AT87200183T patent/ATE81505T1/de not_active IP Right Cessation
- 1987-02-07 DE DE8787200183T patent/DE3782182T2/de not_active Expired - Lifetime
- 1987-02-10 CA CA000529377A patent/CA1336597C/en not_active Expired - Fee Related
- 1987-02-10 WO PCT/JP1987/000086 patent/WO1987006226A2/en unknown
- 1987-02-10 AU AU70207/87A patent/AU601402B2/en not_active Ceased
- 1987-02-10 KR KR1019870701153A patent/KR910000164B1/ko not_active Expired
- 1987-02-11 AR AR87306713A patent/AR245107A1/es active
- 1987-02-12 CN CN91109720A patent/CN1020605C/zh not_active Expired - Lifetime
- 1987-02-12 CN CN87100666A patent/CN1018452B/zh not_active Expired
- 1987-11-18 US US07/131,193 patent/US4882359A/en not_active Expired - Lifetime
- 1987-12-07 SU SU874203780A patent/SU1748644A3/ru active
-
1989
- 1989-02-13 SU SU894613462A patent/SU1750422A3/ru active
- 1989-02-27 SU SU894613514A patent/SU1750423A3/ru active
-
1993
- 1993-01-13 GR GR930400029T patent/GR3006768T3/el unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4450102A (en) | 1982-11-02 | 1984-05-22 | Phillips Petroleum Company | Sulfur based metal cleaners and corrosion inhibitors |
Also Published As
Publication number | Publication date |
---|---|
EP0241050B1 (en) | 1992-10-14 |
JPS62238261A (ja) | 1987-10-19 |
AR245107A1 (es) | 1993-12-30 |
US4882359A (en) | 1989-11-21 |
CN1018452B (zh) | 1992-09-30 |
DE3782182D1 (de) | 1992-11-19 |
EP0241050A3 (en) | 1988-12-28 |
KR880701227A (ko) | 1988-07-26 |
SU1748644A3 (ru) | 1992-07-15 |
WO1987006226A3 (en) | 1988-04-07 |
AU601402B2 (en) | 1990-09-13 |
SU1750422A3 (ru) | 1992-07-23 |
AU7020787A (en) | 1987-11-09 |
ES2046196T3 (es) | 1994-02-01 |
GR3006768T3 (en]) | 1993-06-30 |
DE3782182T2 (de) | 1993-02-25 |
EP0241050A2 (en) | 1987-10-14 |
CN1060287A (zh) | 1992-04-15 |
CN1020605C (zh) | 1993-05-12 |
CA1336597C (en) | 1995-08-08 |
KR910000164B1 (ko) | 1991-01-21 |
ATE81505T1 (de) | 1992-10-15 |
CN87100666A (zh) | 1987-10-21 |
WO1987006226A2 (en) | 1987-10-22 |
SU1750423A3 (ru) | 1992-07-23 |
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