JPH08507790A

JPH08507790A - 大環状カルバメート免疫調節剤

大環状カルバメート免疫調節剤

Info

Publication number: JPH08507790A
Authority: JP; Japan
Prior art keywords: twenty; group; compound; alkyl; hydroxy
Prior art date: 1993-03-17
Legal status : Pending

Application number

JP6521150A

Other languages

English (en)

Japanese (ja)

Inventor

オア，ヤツト・サン

ラリー，ジエイ・アール

Original Assignee

アボツト・ラボラトリーズ

Priority date

1993-03-17

Filing date

1994-03-14

Publication date

1996-08-20

1994-03-14 Application filed by アボツト・ラボラトリーズ filed Critical アボツト・ラボラトリーズ

1996-08-20 Publication of JPH08507790A publication Critical patent/JPH08507790A/ja

Status Pending legal-status Critical Current

Links

239000002955 immunomodulating agent Substances 0.000 title description 3
229940121354 immunomodulator Drugs 0.000 title description 3
230000002584 immunomodulator Effects 0.000 title description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 192
238000000034 method Methods 0.000 claims abstract description 77
239000001257 hydrogen Substances 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
150000002148 esters Chemical class 0.000 claims abstract description 12
150000001408 amides Chemical class 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 55
-1 chlorpropylmethyl Chemical group 0.000 claims description 42
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
201000010099 disease Diseases 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
230000001404 mediated effect Effects 0.000 claims description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
210000000056 organ Anatomy 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
230000003463 hyperproliferative effect Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
230000000302 ischemic effect Effects 0.000 claims description 4
230000000414 obstructive effect Effects 0.000 claims description 4
230000002441 reversible effect Effects 0.000 claims description 4
230000002757 inflammatory effect Effects 0.000 claims description 3
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208000023504 respiratory system disease Diseases 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
229910000077 silane Inorganic materials 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
208000026278 immune system disease Diseases 0.000 claims 2
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
230000001506 immunosuppresive effect Effects 0.000 abstract description 16
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230000000843 anti-fungal effect Effects 0.000 abstract description 6
150000002678 macrocyclic compounds Chemical class 0.000 abstract description 6
230000000845 anti-microbial effect Effects 0.000 abstract description 5
230000000840 anti-viral effect Effects 0.000 abstract description 5
238000002560 therapeutic procedure Methods 0.000 abstract description 3
FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 abstract 1
235000006716 Broussonetia kazinoki Nutrition 0.000 abstract 1
240000006248 Broussonetia kazinoki Species 0.000 abstract 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 53
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 33
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 33
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 26
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QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
ZDQSOHOQTUFQEM-NURRSENYSA-N ascomycin Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-NURRSENYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
229960001967 tacrolimus Drugs 0.000 description 14
239000003795 chemical substances by application Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
230000000694 effects Effects 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
239000003018 immunosuppressive agent Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
208000006673 asthma Diseases 0.000 description 8
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239000002253 acid Substances 0.000 description 7
ZDQSOHOQTUFQEM-XCXYXIJFSA-N ascomycin Natural products CC[C@H]1C=C(C)C[C@@H](C)C[C@@H](OC)[C@H]2O[C@@](O)([C@@H](C)C[C@H]2OC)C(=O)C(=O)N3CCCC[C@@H]3C(=O)O[C@H]([C@H](C)[C@@H](O)CC1=O)C(=C[C@@H]4CC[C@@H](O)[C@H](C4)OC)C ZDQSOHOQTUFQEM-XCXYXIJFSA-N 0.000 description 7
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
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