TW294652B - - Google Patents

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Publication number: TW294652B
Authority: TW; Taiwan
Prior art keywords: cyano; cyclohexane; formula; methyl; cyclopropylmethoxy
Prior art date: 1973-03-05

Application number

TW82104962A

Other languages

English (en)

Chinese (zh)

Original Assignee

Smithkline Beecham Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-03-05

Filing date

1993-06-22

Publication date

1997-01-01

1993-06-22 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

1997-01-01 Application granted granted Critical

1997-01-01 Publication of TW294652B publication Critical patent/TW294652B/zh

Links

-1 2 -cyclopropyl Chemical group 0.000 claims description 160
150000001875 compounds Chemical class 0.000 claims description 133
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 69
125000000217 alkyl group Chemical group 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 22
238000011282 treatment Methods 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 18
235000019000 fluorine Nutrition 0.000 claims description 16
239000007789 gas Substances 0.000 claims description 15
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000001153 fluoro group Chemical group F* 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
239000013589 supplement Substances 0.000 claims description 7
241000700199 Cavia porcellus Species 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
206010061218 Inflammation Diseases 0.000 claims description 3
235000013405 beer Nutrition 0.000 claims description 3
230000004054 inflammatory process Effects 0.000 claims description 3
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
VGZUQDVRGUCGLE-UHFFFAOYSA-N aminomethanol;methane Chemical compound C.NCO VGZUQDVRGUCGLE-UHFFFAOYSA-N 0.000 claims description 2
235000021028 berry Nutrition 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims description 2
238000002512 chemotherapy Methods 0.000 claims description 2
230000008030 elimination Effects 0.000 claims description 2
238000003379 elimination reaction Methods 0.000 claims description 2
238000007639 printing Methods 0.000 claims description 2
239000002689 soil Substances 0.000 claims 7
108010081348 HRT1 protein Hairy Proteins 0.000 claims 5
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
OTWXZYSNQOXADE-UHFFFAOYSA-N 1-(cyclopropylmethoxy)-2-methoxybenzene Chemical compound COC1=CC=CC=C1OCC1CC1 OTWXZYSNQOXADE-UHFFFAOYSA-N 0.000 claims 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 claims 1
241000722267 Regulus satrapa Species 0.000 claims 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
230000000973 chemotherapeutic effect Effects 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
CHXARDKIHSVFDK-UHFFFAOYSA-N hexylphosphane Chemical compound CCCCCCP CHXARDKIHSVFDK-UHFFFAOYSA-N 0.000 claims 1
238000001802 infusion Methods 0.000 claims 1
235000012054 meals Nutrition 0.000 claims 1
229940095102 methyl benzoate Drugs 0.000 claims 1
239000000344 soap Substances 0.000 claims 1
XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 116
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 79
229910052786 argon Inorganic materials 0.000 description 68
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
239000000203 mixture Substances 0.000 description 55
239000007787 solid Substances 0.000 description 48
108060008682 Tumor Necrosis Factor Proteins 0.000 description 43
102100040247 Tumor necrosis factor Human genes 0.000 description 43
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
238000002844 melting Methods 0.000 description 38
230000008018 melting Effects 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
238000004364 calculation method Methods 0.000 description 36
239000000243 solution Substances 0.000 description 36
238000004458 analytical method Methods 0.000 description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 27
201000010099 disease Diseases 0.000 description 25
239000000284 extract Substances 0.000 description 24
238000000034 method Methods 0.000 description 23
210000004027 cell Anatomy 0.000 description 21
229910052943 magnesium sulfate Inorganic materials 0.000 description 21
235000019341 magnesium sulphate Nutrition 0.000 description 21
241000124008 Mammalia Species 0.000 description 18
241000725303 Human immunodeficiency virus Species 0.000 description 17
241000700605 Viruses Species 0.000 description 17
230000000694 effects Effects 0.000 description 17
238000004519 manufacturing process Methods 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
125000004435 hydrogen atom Chemical class [H]* 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
238000003818 flash chromatography Methods 0.000 description 13
230000002401 inhibitory effect Effects 0.000 description 13
239000002904 solvent Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
210000001744 T-lymphocyte Anatomy 0.000 description 12
230000001404 mediated effect Effects 0.000 description 12
102000004127 Cytokines Human genes 0.000 description 11
108090000695 Cytokines Proteins 0.000 description 11
239000011737 fluorine Substances 0.000 description 11
229910052731 fluorine Inorganic materials 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
208000006673 asthma Diseases 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
206010017533 Fungal infection Diseases 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
210000002540 macrophage Anatomy 0.000 description 9
125000003226 pyrazolyl group Chemical group 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
230000004913 activation Effects 0.000 description 8
208000015181 infectious disease Diseases 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
238000010992 reflux Methods 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
208000031886 HIV Infections Diseases 0.000 description 7
108010002352 Interleukin-1 Proteins 0.000 description 7
239000002585 base Substances 0.000 description 7
230000002079 cooperative effect Effects 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 7
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 7
125000001425 triazolyl group Chemical group 0.000 description 7
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
241000282412 Homo Species 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
240000004808 Saccharomyces cerevisiae Species 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
238000011049 filling Methods 0.000 description 6
125000000524 functional group Chemical group 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
238000001727 in vivo Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
125000000335 thiazolyl group Chemical group 0.000 description 6
206010006895 Cachexia Diseases 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
208000031888 Mycoses Diseases 0.000 description 5
206010040070 Septic Shock Diseases 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine group Chemical group [C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
229910052797 bismuth Inorganic materials 0.000 description 5
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000007903 gelatin capsule Substances 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
125000002883 imidazolyl group Chemical group 0.000 description 5
238000009434 installation Methods 0.000 description 5
238000002386 leaching Methods 0.000 description 5
210000001616 monocyte Anatomy 0.000 description 5
210000000440 neutrophil Anatomy 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
230000006433 tumor necrosis factor production Effects 0.000 description 5
208000030507 AIDS Diseases 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
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206010020751 Hypersensitivity Diseases 0.000 description 4
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 4
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000006044 T cell activation Effects 0.000 description 4
208000036142 Viral infection Diseases 0.000 description 4
230000009471 action Effects 0.000 description 4
210000005091 airway smooth muscle Anatomy 0.000 description 4
150000001299 aldehydes Chemical group 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
125000002541 furyl group Chemical group 0.000 description 4
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
210000005087 mononuclear cell Anatomy 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 4
125000005592 polycycloalkyl group Polymers 0.000 description 4
125000000168 pyrrolyl group Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000010076 replication Effects 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
230000009385 viral infection Effects 0.000 description 4
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 3
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SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
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NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
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238000011161 development Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 3
125000002757 morpholinyl group Chemical group 0.000 description 3
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MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 2
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

TW82104962A 1973-03-05 1993-06-22 TW294652B (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US19919373A	1973-03-05	1973-03-05
US86203092A	1992-04-02	1992-04-02
US96876292A	1992-10-30	1992-10-30

Publications (1)

Publication Number	Publication Date
TW294652B true TW294652B (de)	1997-01-01

Family

ID=51565212

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW82104962A TW294652B (de)	1973-03-05	1993-06-22

Country Status (1)

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TW (1)	TW294652B (de)

1993
- 1993-06-22 TW TW82104962A patent/TW294652B/zh not_active IP Right Cessation

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CZ283425B6 (cs)	1998-04-15	Fenylové deriváty a farmaceutické prostředky s jejich obsahem
JPH08507039A (ja)	1996-07-30	アレルギーまたは炎症疾患の治療用化合物
JPH07508261A (ja)	1995-09-14	アレルギーおよび炎症疾患の治療用化合物
JPH09510213A (ja)	1997-10-14	シアノ化合物およびその製造方法
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JPH09503505A (ja)	1997-04-08	化合物、組成物ならびにアレルギーおよび炎症の治療
TW294652B (de)	1997-01-01
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JPH10511391A (ja)	1998-11-04	３，３−（二置換）シクロヘキサン−１−オール二量体および関連化合物
JPH10511387A (ja)	1998-11-04	１，３，３−（三置換）シクロヘキサンダイマーおよび関連化合物
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WO1996010567A1 (en)	1996-04-11	Aminoketone derivative, physiologically acceptable salt thereof, and use of the same
JPH10511656A (ja)	1998-11-10	４，４−（二置換）シクロヘキサン−１−イリジンアセテート二量体および関連化合物
JP2002516601A (ja)	2002-06-04	４，４−（二置換）シクロヘキサン−１−オン単量体および関連化合物
JPH10511659A (ja)	1998-11-10	１，４，４−（三置換）シクロヘキサン単量体および関連する化合物
JPH10511388A (ja)	1998-11-04	３，３−（二置換）シクロヘキサン−１−カルボキシレートダイマーおよび関連化合物
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