CN1546472A - 吡啶基链烷烃-和吡啶基链炔径-酸酰胺作为细胞抑制剂和免疫抑制剂 - Google Patents

吡啶基链烷烃-和吡啶基链炔径-酸酰胺作为细胞抑制剂和免疫抑制剂 Download PDF

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Publication number: CN1546472A
Authority: CN; China
Prior art keywords: group; alkyl; base; dihydro; carbonyl
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.): Pending

Application number

CNA2004100325866A

Other languages

English (en)

Chinese (zh)

Inventor

��ơ��

埃尔菲·比德曼

马克思·哈斯曼

罗兰·莱塞

̩

本诺·拉泰尔

弗里德曼·赖特

�ɳ��

巴巴拉·沙因

克劳斯·塞贝尔

�ָ��

克劳斯·沃格特

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

Klinge Pharma GmbH and Co

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

2004-11-17

1997-06-20 Application filed by Klinge Pharma GmbH and Co filed Critical Klinge Pharma GmbH and Co

2004-11-17 Publication of CN1546472A publication Critical patent/CN1546472A/zh

Status Pending legal-status Critical Current

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-1 Pyridyl alkane acid amides Chemical class 0.000 title claims abstract description 261
239000000824 cytostatic agent Substances 0.000 title claims description 14
230000001085 cytostatic effect Effects 0.000 title claims description 14
230000001506 immunosuppresive effect Effects 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 132
239000003814 drug Substances 0.000 claims abstract description 50
238000000034 method Methods 0.000 claims abstract description 36
238000004519 manufacturing process Methods 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims description 129
229910052739 hydrogen Inorganic materials 0.000 claims description 129
125000003118 aryl group Chemical group 0.000 claims description 88
239000000203 mixture Substances 0.000 claims description 88
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 83
150000002431 hydrogen Chemical class 0.000 claims description 80
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
125000004076 pyridyl group Chemical group 0.000 claims description 50
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 48
150000003053 piperidines Chemical class 0.000 claims description 48
241000534944 Thia Species 0.000 claims description 47
125000004432 carbon atom Chemical group C* 0.000 claims description 47
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 46
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
239000000463 material Substances 0.000 claims description 44
238000002360 preparation method Methods 0.000 claims description 42
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 38
229910052731 fluorine Inorganic materials 0.000 claims description 36
125000004093 cyano group Chemical group *C#N 0.000 claims description 34
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 33
125000000304 alkynyl group Chemical group 0.000 claims description 33
239000011737 fluorine Substances 0.000 claims description 33
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
229910052736 halogen Inorganic materials 0.000 claims description 32
150000002367 halogens Chemical class 0.000 claims description 30
125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
229910052760 oxygen Inorganic materials 0.000 claims description 27
125000005605 benzo group Chemical group 0.000 claims description 26
229910052799 carbon Inorganic materials 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 21
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 20
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
239000001301 oxygen Substances 0.000 claims description 19
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 18
238000005984 hydrogenation reaction Methods 0.000 claims description 18
229920006395 saturated elastomer Polymers 0.000 claims description 18
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
125000001624 naphthyl group Chemical group 0.000 claims description 14
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
229940079593 drug Drugs 0.000 claims description 11
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 11
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 11
125000001544 thienyl group Chemical group 0.000 claims description 11
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
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 10
QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
125000000468 ketone group Chemical group 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 9
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 9
239000004913 cyclooctene Substances 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
239000003018 immunosuppressive agent Substances 0.000 claims description 9
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 9
241000790917 Dioxys <bee> Species 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 8
125000001118 alkylidene group Chemical group 0.000 claims description 8
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 8
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 8
125000002541 furyl group Chemical group 0.000 claims description 8
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
239000011707 mineral Substances 0.000 claims description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
125000005493 quinolyl group Chemical group 0.000 claims description 8
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 7
AFVDZBIIBXWASR-AATRIKPKSA-N (E)-1,3,5-hexatriene Chemical compound C=C\C=C\C=C AFVDZBIIBXWASR-AATRIKPKSA-N 0.000 claims description 7
OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims description 7
GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 7
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 7
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 7
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 7
125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 claims description 6
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 6
125000003302 alkenyloxy group Chemical group 0.000 claims description 6
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 6
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 6
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
238000002156 mixing Methods 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 5
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 5
IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims description 5
AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims description 5
UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical compound C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 claims description 5
CZWWCTHQXBMHDA-UHFFFAOYSA-N 3h-1,3-thiazol-2-one Chemical compound OC1=NC=CS1 CZWWCTHQXBMHDA-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 5
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 5
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
239000002671 adjuvant Substances 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 5
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 5
125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 5
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 5
239000012964 benzotriazole Substances 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical compound C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 claims description 5
125000005046 dihydronaphthyl group Chemical group 0.000 claims description 5
239000002552 dosage form Substances 0.000 claims description 5
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 5
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 5
125000005956 isoquinolyl group Chemical group 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
238000007254 oxidation reaction Methods 0.000 claims description 5
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
125000002098 pyridazinyl group Chemical group 0.000 claims description 5
125000005554 pyridyloxy group Chemical group 0.000 claims description 5
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 5
125000004306 triazinyl group Chemical group 0.000 claims description 5
125000001425 triazolyl group Chemical group 0.000 claims description 5
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000006795 (C2-C7) alkoxycarbonyloxy group Chemical group 0.000 claims description 4
125000004761 (C2-C7) alkylaminocarbonyl group Chemical group 0.000 claims description 4
125000004763 (C3-C13) dialkylaminocarbonyl group Chemical group 0.000 claims description 4
KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 4
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 claims description 4
XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 4
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 4
CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 4
IDUSJBBWEKNWAK-UHFFFAOYSA-N 3,4-dihydro-2h-1,2-benzothiazine Chemical compound C1=CC=C2SNCCC2=C1 IDUSJBBWEKNWAK-UHFFFAOYSA-N 0.000 claims description 4
GYLMCBOAXJVARF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptane Chemical compound C1C2CCC1NC2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 claims description 4
SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims description 4
DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000005108 alkenylthio group Chemical group 0.000 claims description 4
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 4
239000002246 antineoplastic agent Substances 0.000 claims description 4
UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 4
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 4
125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
125000005945 imidazopyridyl group Chemical group 0.000 claims description 4
150000002475 indoles Chemical class 0.000 claims description 4
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 4
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims description 4
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 4
150000003016 phosphoric acids Chemical class 0.000 claims description 4
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 4
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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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Catalysts (AREA)

CNA2004100325866A 1996-06-20 1997-06-20 吡啶基链烷烃-和吡啶基链炔径-酸酰胺作为细胞抑制剂和免疫抑制剂 Pending CN1546472A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19624659.8		1996-06-20
DE19624659A DE19624659A1 (de)	1996-06-20	1996-06-20	Neue Pyridylalken- und Pyridylalkinsäureamide

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CNB971974241A Division CN1152032C (zh)	1996-06-20	1997-06-20	吡啶基链烷烃-和吡啶基链炔径-酸酰胺作为细胞抑制剂和免疫抑制剂

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CN1546472A true CN1546472A (zh)	2004-11-17

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ID=7797501

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Application Number	Title	Priority Date	Filing Date
CNA2004100325866A Pending CN1546472A (zh)	1996-06-20	1997-06-20	吡啶基链烷烃-和吡啶基链炔径-酸酰胺作为细胞抑制剂和免疫抑制剂
CNB971974241A Expired - Fee Related CN1152032C (zh)	1996-06-20	1997-06-20	吡啶基链烷烃-和吡啶基链炔径-酸酰胺作为细胞抑制剂和免疫抑制剂

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CNB971974241A Expired - Fee Related CN1152032C (zh)	1996-06-20	1997-06-20	吡啶基链烷烃-和吡啶基链炔径-酸酰胺作为细胞抑制剂和免疫抑制剂

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US (3)	US7241745B2 (2)
EP (1)	EP0923570B1 (2)
JP (1)	JP4225572B2 (2)
CN (2)	CN1546472A (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)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN107827897A (zh) *	2017-10-23	2018-03-23	青岛大学	一种手性七元螺环吲哚酮类化合物的合成方法
CN108558840A (zh) *	2018-06-04	2018-09-21	上海交通大学	水溶性氮杂α-萘黄酮类化合物及其制备方法和医药用途

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19624659A1 (de) *	1996-06-20	1998-01-08	Klinge Co Chem Pharm Fab	Neue Pyridylalken- und Pyridylalkinsäureamide
DE19756261A1 (de) *	1997-12-17	1999-07-01	Klinge Co Chem Pharm Fab	Neue arylsubstituierte Pyridylalkan-, alken- und alkincarbonsäureamide
DE19756235A1 (de) *	1997-12-17	1999-07-01	Klinge Co Chem Pharm Fab	Neue piperidinylsubstituierte Pyridylalkan- alken- und -alkincarbonsäureamide
DE19756212A1 (de) *	1997-12-17	1999-07-01	Klinge Co Chem Pharm Fab	Neue, mit einem cyclischen Imid substituierte Pyridylalkan-, alken- und -alkincarbonsäureamide
DE19756236A1 (de) *	1997-12-17	1999-07-01	Klinge Co Chem Pharm Fab	Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide
DE19818044A1 (de) *	1998-04-22	1999-10-28	Klinge Co Chem Pharm Fab	Verwendung von Vitamin-PP-Verbindungen
DE69921351T2 (de) *	1998-11-17	2006-03-09	F. Hoffmann-La Roche Ag	4-Aroyl-Piperidin-CCR-3 Rezeptorantagonisten III
EP1031564A1 (en) *	1999-02-26	2000-08-30	Klinge Pharma GmbH	Inhibitors of cellular nicotinamide mononucleotide formation and their use in cancer therapy
US6432432B1 (en)	1999-03-05	2002-08-13	Arch Chemicals, Inc.	Chemical method of making a suspension, emulsion or dispersion of pyrithione particles
CO5180550A1 (es)	1999-04-19	2002-07-30	Smithkline Beecham Corp	Inhibidores de fab i
CO5370679A1 (es)	1999-06-01	2004-02-27	Smithkline Beecham Corp	Inhibidores fab 1
ATE285821T1 (de) *	1999-10-08	2005-01-15	Affinium Pharm Inc	Fab i inhibitoren
US6730684B1 (en)	1999-10-08	2004-05-04	Affinium Pharmaceuticals, Inc.	Fab I inhibitors
US6762201B1 (en)	1999-10-08	2004-07-13	Affinium Pharmaceuticals, Inc.	Fab I inhibitors
CA2444597A1 (en)	2001-04-06	2002-10-06	Affinium Pharmaceuticals, Inc.	Fab i inhibitors
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1996
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1997
- 1997-06-19 ZA ZA9705437A patent/ZA975437B/xx unknown
- 1997-06-20 BR BRPI9709823-0B1A patent/BR9709823B1/pt not_active IP Right Cessation
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- 1997-06-20 CN CNA2004100325866A patent/CN1546472A/zh active Pending
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- 1997-06-20 AT AT97928261T patent/ATE224888T1/de active
- 1997-06-20 ES ES97928261T patent/ES2179351T3/es not_active Expired - Lifetime
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2006
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DE69715888D1 (de)	2002-10-31
ATE224888T1 (de)	2002-10-15
ES2179351T3 (es)	2003-01-16
CA2257448C (en)	2008-08-19
IL127352A0 (en)	1999-10-28
DK0923570T3 (da)	2003-01-20
JP4225572B2 (ja)	2009-02-18
CA2257448A1 (en)	1997-12-24
WO1997048696A1 (en)	1997-12-24
US20070142377A1 (en)	2007-06-21
CZ291791B6 (cs)	2003-05-14
HK1021974A1 (en)	2000-07-21
JP2000516913A (ja)	2000-12-19
EP0923570A1 (en)	1999-06-23
HU225715B1 (en)	2007-07-30
CN1152032C (zh)	2004-06-02
AU3262597A (en)	1998-01-07
ZA975437B (en)	1998-02-10
PT923570E (pt)	2002-12-31
HUP9903766A2 (en)	2000-09-28
BR9709823A (pt)	1999-08-10
US7241745B2 (en)	2007-07-10
DE69715888T2 (de)	2003-07-31
US20070219197A1 (en)	2007-09-20
TR199802651T2 (xx)	1999-04-21
RU2200734C2 (ru)	2003-03-20
IL127352A (en)	2003-10-31
CN1228777A (zh)	1999-09-15
AU736206B2 (en)	2001-07-26
EP0923570B1 (en)	2002-09-25
BR9709823B1 (pt)	2013-09-17
DE19624659A1 (de)	1998-01-08
US20030162972A1 (en)	2003-08-28
CZ409398A3 (cs)	1999-05-12
HUP9903766A3 (en)	2000-12-28

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CN1546472A - 吡啶基链烷烃-和吡啶基链炔径-酸酰胺作为细胞抑制剂和免疫抑制剂 - Google Patents

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