JP4225572B2 - 細胞増殖抑制剤および免疫抑制剤としてのピリジルアルケン―およびピリジルアルキン―酸アミド類 - Google Patents

細胞増殖抑制剤および免疫抑制剤としてのピリジルアルケン―およびピリジルアルキン―酸アミド類 Download PDF

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Publication number: JP4225572B2
Authority: JP; Japan
Prior art keywords: hydrogen; group; alkyl; hydroxy; compound
Prior art date: 1996-06-20
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 - Fee Related

Application number

JP50231898A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000516913A5 (2

JP2000516913A (ja

Inventor

エルフィビエデルマン

マックスハスマン

ローランドローセル

ベンノラッテル

フリードマンレイテル

バーバラスチェイン

クラウスセイベル

クラウスボークト

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Astellas Deutschland GmbH

Original Assignee

Astellas Deutschland GmbH

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.)

1996-06-20

Filing date

1997-06-20

Publication date

2009-02-18

1997-06-20 Application filed by Astellas Deutschland GmbH filed Critical Astellas Deutschland GmbH

2000-12-19 Publication of JP2000516913A publication Critical patent/JP2000516913A/ja

2005-02-10 Publication of JP2000516913A5 publication Critical patent/JP2000516913A5/ja

2009-02-18 Application granted granted Critical

2009-02-18 Publication of JP4225572B2 publication Critical patent/JP4225572B2/ja

2017-06-20 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000824 cytostatic agent Substances 0.000 title claims description 13
230000001085 cytostatic effect Effects 0.000 title claims description 11
239000003018 immunosuppressive agent Substances 0.000 title claims description 6
229940125721 immunosuppressive agent Drugs 0.000 title claims description 5
-1 pyridyl alkene Chemical class 0.000 claims abstract description 386
150000001875 compounds Chemical class 0.000 claims abstract description 152
238000000034 method Methods 0.000 claims abstract description 29
239000003814 drug Substances 0.000 claims abstract description 28
238000011282 treatment Methods 0.000 claims abstract description 27
206010028980 Neoplasm Diseases 0.000 claims abstract description 25
238000004519 manufacturing process Methods 0.000 claims abstract description 21
230000001506 immunosuppresive effect Effects 0.000 claims abstract description 10
206010062016 Immunosuppression Diseases 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 141
239000001257 hydrogen Substances 0.000 claims description 141
150000002431 hydrogen Chemical class 0.000 claims description 86
239000000203 mixture Substances 0.000 claims description 84
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 79
125000003118 aryl group Chemical group 0.000 claims description 69
239000004480 active ingredient Substances 0.000 claims description 67
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
239000000243 solution Substances 0.000 claims description 53
239000002904 solvent Substances 0.000 claims description 53
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 49
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 48
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
238000006243 chemical reaction Methods 0.000 claims description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 42
229910052757 nitrogen Inorganic materials 0.000 claims description 42
125000000217 alkyl group Chemical group 0.000 claims description 41
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 40
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 36
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 33
229910052736 halogen Inorganic materials 0.000 claims description 32
150000002367 halogens Chemical class 0.000 claims description 32
125000006413 ring segment Chemical group 0.000 claims description 32
239000011737 fluorine Substances 0.000 claims description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
239000002585 base Substances 0.000 claims description 29
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 28
238000009472 formulation Methods 0.000 claims description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
125000004093 cyano group Chemical group *C#N 0.000 claims description 27
239000000843 powder Substances 0.000 claims description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
229910052731 fluorine Inorganic materials 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 24
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 23
125000005842 heteroatom Chemical group 0.000 claims description 23
239000003826 tablet Substances 0.000 claims description 23
239000002671 adjuvant Substances 0.000 claims description 22
239000008194 pharmaceutical composition Substances 0.000 claims description 22
125000004076 pyridyl group Chemical group 0.000 claims description 22
SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 19
239000000725 suspension Substances 0.000 claims description 19
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 18
125000001624 naphthyl group Chemical group 0.000 claims description 18
229910052760 oxygen Inorganic materials 0.000 claims description 17
NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 claims description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
229940079593 drug Drugs 0.000 claims description 16
239000000443 aerosol Substances 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 15
239000003380 propellant Substances 0.000 claims description 15
229920006395 saturated elastomer Polymers 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 14
238000000746 purification Methods 0.000 claims description 14
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 13
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 13
125000004122 cyclic group Chemical group 0.000 claims description 13
125000002541 furyl group Chemical group 0.000 claims description 13
125000001041 indolyl group Chemical group 0.000 claims description 13
125000005493 quinolyl group Chemical group 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000001544 thienyl group Chemical group 0.000 claims description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 12
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
125000002883 imidazolyl group Chemical group 0.000 claims description 12
125000004043 oxo group Chemical group O=* 0.000 claims description 12
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 12
239000007787 solid Substances 0.000 claims description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 11
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 11
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
239000008101 lactose Substances 0.000 claims description 11
125000001715 oxadiazolyl group Chemical group 0.000 claims description 11
125000002971 oxazolyl group Chemical group 0.000 claims description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
125000001113 thiadiazolyl group Chemical group 0.000 claims description 11
125000000335 thiazolyl group Chemical group 0.000 claims description 11
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 10
238000002347 injection Methods 0.000 claims description 10
239000007924 injection Substances 0.000 claims description 10
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
150000001735 carboxylic acids Chemical class 0.000 claims description 9
239000000839 emulsion Substances 0.000 claims description 9
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 9
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 9
125000003373 pyrazinyl group Chemical group 0.000 claims description 9
125000003226 pyrazolyl group Chemical group 0.000 claims description 9
125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 9
230000001225 therapeutic effect Effects 0.000 claims description 9
150000008064 anhydrides Chemical class 0.000 claims description 8
239000002674 ointment Substances 0.000 claims description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 7
UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
241000282414 Homo sapiens Species 0.000 claims description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 7
125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 7
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
239000000969 carrier Substances 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
210000004051 gastric juice Anatomy 0.000 claims description 7
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 7
125000005956 isoquinolyl group Chemical group 0.000 claims description 7
125000001786 isothiazolyl group Chemical group 0.000 claims description 7
125000000842 isoxazolyl group Chemical group 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
230000036961 partial effect Effects 0.000 claims description 7
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 7
125000002098 pyridazinyl group Chemical group 0.000 claims description 7
125000000168 pyrrolyl group Chemical group 0.000 claims description 7
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 7
LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 7
125000001425 triazolyl group Chemical group 0.000 claims description 7
239000008096 xylene Substances 0.000 claims description 7
125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 6
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical group FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 6
CVEXTAUZJWYDJX-UHFFFAOYSA-N 1,3,4,10-Tetrahydro-9(2H)-acridinone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1CCCC2 CVEXTAUZJWYDJX-UHFFFAOYSA-N 0.000 claims description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
VWBYXJRDIQCSLW-UHFFFAOYSA-N O=[P](c1ccccc1)c1ccccc1 Chemical group O=[P](c1ccccc1)c1ccccc1 VWBYXJRDIQCSLW-UHFFFAOYSA-N 0.000 claims description 6
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 6
125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 claims description 6
125000005046 dihydronaphthyl group Chemical group 0.000 claims description 6
125000005945 imidazopyridyl group Chemical group 0.000 claims description 6
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 6
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 5
CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 claims description 5
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 5
GYLMCBOAXJVARF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptane Chemical compound C1C2CCC1NC2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 claims description 5
SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims description 5
DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 claims description 5
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims description 5
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 5
125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 5
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims description 5
125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 5
125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 5
239000008103 glucose Substances 0.000 claims description 5
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 5
239000007943 implant Substances 0.000 claims description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
AQNQGBUEVCAVML-UHFFFAOYSA-N oxazepane Chemical compound C1CCNOCC1 AQNQGBUEVCAVML-UHFFFAOYSA-N 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
239000007921 spray Substances 0.000 claims description 5
125000004306 triazinyl group Chemical group 0.000 claims description 5
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 claims description 4
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150000002118 epoxides Chemical group 0.000 claims description 2
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230000002496 gastric effect Effects 0.000 claims description 2
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OZDDODZSMNLZCZ-UHFFFAOYSA-N n-[4-(1-methylsulfonylpiperidin-4-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C1CN(S(=O)(=O)C)CCC1CCCCNC(=O)C=CC1=CC=CN=C1 OZDDODZSMNLZCZ-UHFFFAOYSA-N 0.000 claims description 2
WJXXCPFHNISDFK-UHFFFAOYSA-N n-[4-(1-naphthalen-2-ylsulfonylpiperidin-4-yl)butyl]-5-pyridin-3-ylpenta-2,4-dienamide Chemical compound C1CN(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)CCC1CCCCNC(=O)C=CC=CC1=CC=CN=C1 WJXXCPFHNISDFK-UHFFFAOYSA-N 0.000 claims description 2
GRTBFFDLPDANJH-UHFFFAOYSA-N n-[4-[1-(3,3-diphenylpropanoyl)piperidin-4-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCC(CC1)CCN1C(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 GRTBFFDLPDANJH-UHFFFAOYSA-N 0.000 claims description 2
UVKJVMWMNOUONH-UHFFFAOYSA-N n-[4-[1-(5,6-dihydrobenzo[b][1]benzazepine-11-carbonyl)piperidin-4-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C1CN(C(=O)N2C3=CC=CC=C3CCC3=CC=CC=C32)CCC1CCCCNC(=O)C=CC1=CC=CN=C1 UVKJVMWMNOUONH-UHFFFAOYSA-N 0.000 claims description 2
BYKSXKZTLDOGMU-UHFFFAOYSA-N n-[4-[1-(6,11-dihydrobenzo[c][1]benzoxepin-11-yl)piperidin-4-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C1CN(C2C3=CC=CC=C3OCC3=CC=CC=C32)CCC1CCCCNC(=O)C=CC1=CC=CN=C1 BYKSXKZTLDOGMU-UHFFFAOYSA-N 0.000 claims description 2
SHVXMKWLGXBIAA-UHFFFAOYSA-N n-[4-[1-[phenyl(pyridin-3-yl)methyl]piperidin-4-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCC(CC1)CCN1C(C=1C=NC=CC=1)C1=CC=CC=C1 SHVXMKWLGXBIAA-UHFFFAOYSA-N 0.000 claims description 2
RTGGVVSUNFQQGC-UHFFFAOYSA-N n-[4-[1-[phenyl(pyridin-4-yl)methyl]piperidin-4-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCC(CC1)CCN1C(C=1C=CN=CC=1)C1=CC=CC=C1 RTGGVVSUNFQQGC-UHFFFAOYSA-N 0.000 claims description 2
KYAMVWKIMUMBKN-UHFFFAOYSA-N n-[7-(1-benzhydrylpiperidin-4-yl)heptyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCCCCC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 KYAMVWKIMUMBKN-UHFFFAOYSA-N 0.000 claims description 2
AGGJAKIWECHSCV-UHFFFAOYSA-N n-[8-(1-benzhydrylpiperidin-4-yl)octyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCCCCCC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 AGGJAKIWECHSCV-UHFFFAOYSA-N 0.000 claims description 2
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 2
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125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
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239000000829 suppository Substances 0.000 claims description 2
125000001302 tertiary amino group Chemical group 0.000 claims description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Public Health (AREA)
Biochemistry (AREA)
Immunology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Transplantation (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Hematology (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Catalysts (AREA)

JP50231898A 1996-06-20 1997-06-20 細胞増殖抑制剤および免疫抑制剤としてのピリジルアルケン―およびピリジルアルキン―酸アミド類 Expired - Fee Related JP4225572B2 (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19624659A DE19624659A1 (de)	1996-06-20	1996-06-20	Neue Pyridylalken- und Pyridylalkinsäureamide
DE19624659.8		1996-06-20
PCT/EP1997/003245 WO1997048696A1 (en)	1996-06-20	1997-06-20	Pyridyl alkene- and pyridyl alkine- acid amides as cytostatics and immunosuppressives

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JP2000516913A JP2000516913A (ja)	2000-12-19
JP2000516913A5 JP2000516913A5 (2)	2005-02-10
JP4225572B2 true JP4225572B2 (ja)	2009-02-18

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ID=7797501

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JP50231898A Expired - Fee Related JP4225572B2 (ja)	1996-06-20	1997-06-20	細胞増殖抑制剤および免疫抑制剤としてのピリジルアルケン―およびピリジルアルキン―酸アミド類

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US (3)	US7241745B2 (2)
EP (1)	EP0923570B1 (2)
JP (1)	JP4225572B2 (2)
CN (2)	CN1152032C (2)
AT (1)	ATE224888T1 (2)
AU (1)	AU736206B2 (2)
BR (1)	BR9709823B1 (2)
CA (1)	CA2257448C (2)
CZ (1)	CZ291791B6 (2)
DE (2)	DE19624659A1 (2)
DK (1)	DK0923570T3 (2)
ES (1)	ES2179351T3 (2)
HU (1)	HU225715B1 (2)
IL (1)	IL127352A (2)
PT (1)	PT923570E (2)
RU (1)	RU2200734C2 (2)
TR (1)	TR199802651T2 (2)
WO (1)	WO1997048696A1 (2)
ZA (1)	ZA975437B (2)

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1996
- 1996-06-20 DE DE19624659A patent/DE19624659A1/de not_active Ceased
1997
- 1997-06-19 ZA ZA9705437A patent/ZA975437B/xx unknown
- 1997-06-20 RU RU99101069/04A patent/RU2200734C2/ru not_active IP Right Cessation
- 1997-06-20 PT PT97928261T patent/PT923570E/pt unknown
- 1997-06-20 DE DE69715888T patent/DE69715888T2/de not_active Expired - Lifetime
- 1997-06-20 DK DK97928261T patent/DK0923570T3/da active
- 1997-06-20 EP EP97928261A patent/EP0923570B1/en not_active Expired - Lifetime
- 1997-06-20 TR TR1998/02651T patent/TR199802651T2/xx unknown
- 1997-06-20 CN CNB971974241A patent/CN1152032C/zh not_active Expired - Fee Related
- 1997-06-20 AU AU32625/97A patent/AU736206B2/en not_active Ceased
- 1997-06-20 CN CNA2004100325866A patent/CN1546472A/zh active Pending
- 1997-06-20 BR BRPI9709823-0B1A patent/BR9709823B1/pt not_active IP Right Cessation
- 1997-06-20 CZ CZ19984093A patent/CZ291791B6/cs not_active IP Right Cessation
- 1997-06-20 AT AT97928261T patent/ATE224888T1/de active
- 1997-06-20 WO PCT/EP1997/003245 patent/WO1997048696A1/en not_active Ceased
- 1997-06-20 JP JP50231898A patent/JP4225572B2/ja not_active Expired - Fee Related
- 1997-06-20 ES ES97928261T patent/ES2179351T3/es not_active Expired - Lifetime
- 1997-06-20 HU HU9903766A patent/HU225715B1/hu not_active IP Right Cessation
- 1997-06-20 CA CA002257448A patent/CA2257448C/en not_active Expired - Fee Related
- 1997-06-20 IL IL12735297A patent/IL127352A/xx not_active IP Right Cessation
2002
- 2002-08-05 US US10/213,952 patent/US7241745B2/en not_active Expired - Fee Related
2006
- 2006-12-07 US US11/635,157 patent/US20070219197A1/en not_active Abandoned
2007
- 2007-02-26 US US11/678,980 patent/US20070142377A1/en not_active Abandoned

Also Published As

Publication number	Publication date
AU736206B2 (en)	2001-07-26
DE69715888D1 (de)	2002-10-31
WO1997048696A1 (en)	1997-12-24
CN1228777A (zh)	1999-09-15
CZ409398A3 (cs)	1999-05-12
HU225715B1 (en)	2007-07-30
US20070142377A1 (en)	2007-06-21
BR9709823B1 (pt)	2013-09-17
EP0923570A1 (en)	1999-06-23
US20030162972A1 (en)	2003-08-28
IL127352A0 (en)	1999-10-28
BR9709823A (pt)	1999-08-10
HUP9903766A3 (en)	2000-12-28
HK1021974A1 (en)	2000-07-21
RU2200734C2 (ru)	2003-03-20
JP2000516913A (ja)	2000-12-19
ZA975437B (en)	1998-02-10
CZ291791B6 (cs)	2003-05-14
DE69715888T2 (de)	2003-07-31
EP0923570B1 (en)	2002-09-25
IL127352A (en)	2003-10-31
TR199802651T2 (xx)	1999-04-21
ES2179351T3 (es)	2003-01-16
DE19624659A1 (de)	1998-01-08
DK0923570T3 (da)	2003-01-20
CN1546472A (zh)	2004-11-17
CN1152032C (zh)	2004-06-02
CA2257448C (en)	2008-08-19
ATE224888T1 (de)	2002-10-15
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AU3262597A (en)	1998-01-07
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