ZA200605082B - Novel tricyclic spiroderivatives as modulators of chemokine receptor activity - Google Patents

Novel tricyclic spiroderivatives as modulators of chemokine receptor activity Download PDF

Info

Publication number: ZA200605082B
Authority: ZA; South Africa
Prior art keywords: amino; alkyl; halogen; formula; spiro
Prior art date: 2003-12-22

Application number

ZA200605082A

Other languages

English (en)

Inventor

Hossain Nafizal

Ivanova Svetlana

Original Assignee

Astrazeneca Ab

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.)

2003-12-22

Filing date

2006-06-20

Publication date

2007-11-28

2006-06-20 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2007-11-28 Publication of ZA200605082B publication Critical patent/ZA200605082B/en

Links

230000000694 effects Effects 0.000 title claims description 4
102000009410 Chemokine receptor Human genes 0.000 title claims 2
108050000299 Chemokine receptor Proteins 0.000 title claims 2
-1 cyano, hydroxyl Chemical group 0.000 claims description 79
125000000217 alkyl group Chemical group 0.000 claims description 78
229910052736 halogen Inorganic materials 0.000 claims description 57
150000002367 halogens Chemical class 0.000 claims description 57
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
125000001424 substituent group Chemical group 0.000 claims description 43
125000003545 alkoxy group Chemical group 0.000 claims description 35
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
229910052757 nitrogen Inorganic materials 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 17
125000004122 cyclic group Chemical group 0.000 claims description 16
125000000623 heterocyclic group Chemical group 0.000 claims description 16
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000012453 solvate Substances 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
125000001188 haloalkyl group Chemical group 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
239000005864 Sulphur Substances 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 10
239000003814 drug Substances 0.000 claims 7
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 5
229940090248 4-hydroxybenzoic acid Drugs 0.000 claims 3
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 3
239000004202 carbamide Substances 0.000 claims 2
239000003085 diluting agent Substances 0.000 claims 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
239000002671 adjuvant Substances 0.000 claims 1
230000009286 beneficial effect Effects 0.000 claims 1
230000001684 chronic effect Effects 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
208000027866 inflammatory disease Diseases 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
201000006417 multiple sclerosis Diseases 0.000 claims 1
230000000414 obstructive effect Effects 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
230000002685 pulmonary effect Effects 0.000 claims 1
229960005419 nitrogen Drugs 0.000 description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
125000006413 ring segment Chemical group 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
125000002619 bicyclic group Chemical group 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
108010004073 cysteinylcysteine Proteins 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000011630 iodine Substances 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
102000019034 Chemokines Human genes 0.000 description 3
108010012236 Chemokines Proteins 0.000 description 3
OABOXRPGTFRBFZ-IMJSIDKUSA-N Cys-Cys Chemical compound SC[C@H](N)C(=O)N[C@@H](CS)C(O)=O OABOXRPGTFRBFZ-IMJSIDKUSA-N 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000003367 polycyclic group Chemical group 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 2
125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 2
102000004890 Interleukin-8 Human genes 0.000 description 2
108090001007 Interleukin-8 Proteins 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002975 chemoattractant Substances 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 2
229940096397 interleukin-8 Drugs 0.000 description 2
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
210000000440 neutrophil Anatomy 0.000 description 2
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
235000018102 proteins Nutrition 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
125000000719 pyrrolidinyl group Chemical group 0.000 description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
125000003003 spiro group Chemical group 0.000 description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
102100022718 Atypical chemokine receptor 2 Human genes 0.000 description 1
102100031172 C-C chemokine receptor type 1 Human genes 0.000 description 1
101710149814 C-C chemokine receptor type 1 Proteins 0.000 description 1
102100031151 C-C chemokine receptor type 2 Human genes 0.000 description 1
101710149815 C-C chemokine receptor type 2 Proteins 0.000 description 1
102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 1
101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 1
102100037853 C-C chemokine receptor type 4 Human genes 0.000 description 1
101710149863 C-C chemokine receptor type 4 Proteins 0.000 description 1
102100036301 C-C chemokine receptor type 7 Human genes 0.000 description 1
102100025074 C-C chemokine receptor-like 2 Human genes 0.000 description 1
102100021943 C-C motif chemokine 2 Human genes 0.000 description 1
101710155857 C-C motif chemokine 2 Proteins 0.000 description 1
102100032366 C-C motif chemokine 7 Human genes 0.000 description 1
101710155834 C-C motif chemokine 7 Proteins 0.000 description 1
102100034871 C-C motif chemokine 8 Human genes 0.000 description 1
101710155833 C-C motif chemokine 8 Proteins 0.000 description 1
102100036166 C-X-C chemokine receptor type 1 Human genes 0.000 description 1
102100028989 C-X-C chemokine receptor type 2 Human genes 0.000 description 1
102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 description 1
102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 1
108050006947 CXC Chemokine Proteins 0.000 description 1
102000019388 CXC chemokine Human genes 0.000 description 1
102100032903 Copper chaperone for superoxide dismutase Human genes 0.000 description 1
102100023688 Eotaxin Human genes 0.000 description 1
101710139422 Eotaxin Proteins 0.000 description 1
101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 description 1
101000777558 Homo sapiens C-C chemokine receptor type 10 Proteins 0.000 description 1
101000716068 Homo sapiens C-C chemokine receptor type 6 Proteins 0.000 description 1
101000716065 Homo sapiens C-C chemokine receptor type 7 Proteins 0.000 description 1
101000947174 Homo sapiens C-X-C chemokine receptor type 1 Proteins 0.000 description 1
101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 description 1
101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 description 1
101000868241 Homo sapiens Copper chaperone for superoxide dismutase Proteins 0.000 description 1
108010018951 Interleukin-8B Receptors Proteins 0.000 description 1
101710151805 Mitochondrial intermediate peptidase 1 Proteins 0.000 description 1
102000014962 Monocyte Chemoattractant Proteins Human genes 0.000 description 1
108010064136 Monocyte Chemoattractant Proteins Proteins 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
230000001363 autoimmune Effects 0.000 description 1
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
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 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
208000037765 diseases and disorders Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000009509 drug development Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
230000028993 immune response Effects 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
AEUKDPKXTPNBNY-XEYRWQBLSA-N mcp 2 Chemical compound C([C@@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)C1=CC=CC=C1 AEUKDPKXTPNBNY-XEYRWQBLSA-N 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000007170 pathology Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000005289 uranyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
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ZA200605082A 2003-12-22 2006-06-20 Novel tricyclic spiroderivatives as modulators of chemokine receptor activity ZA200605082B (en)

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SE0303541A SE0303541D0 (sv)	2003-12-22	2003-12-22	New compounds

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US (2)	US7524856B2 (pt)
EP (1)	EP1699791A1 (pt)
JP (1)	JP2007515476A (pt)
KR (1)	KR20060117343A (pt)
CN (1)	CN1918160A (pt)
AR (1)	AR046992A1 (pt)
AU (1)	AU2004303735B2 (pt)
BR (1)	BRPI0417036A (pt)
CA (1)	CA2548494A1 (pt)
IL (1)	IL175958A0 (pt)
MX (1)	MXPA06007025A (pt)
NO (1)	NO20063355L (pt)
SE (1)	SE0303541D0 (pt)
TW (1)	TW200604197A (pt)
UY (1)	UY28694A1 (pt)
WO (1)	WO2005061499A1 (pt)
ZA (1)	ZA200605082B (pt)

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SE0302755D0 (sv)	2003-10-17	2003-10-17	Astrazeneca Ab	Novel compounds
SE0302811D0 (sv)	2003-10-23	2003-10-23	Astrazeneca Ab	Novel compounds
SE0303090D0 (sv) *	2003-11-20	2003-11-20	Astrazeneca Ab	Novel compounds
SE0303280D0 (sv)	2003-12-05	2003-12-05	Astrazeneca Ab	Novel compounds
SE0303541D0 (sv)	2003-12-22	2003-12-22	Astrazeneca Ab	New compounds
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CA2657639A1 (en)	2006-07-19	2008-01-24	Astrazeneca Ab	Novel tricyclic spiropiperidine compounds, their synthesis and their uses as modulators of chemokine receptor activity

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2009
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Also Published As

Publication number	Publication date
UY28694A1 (es)	2005-07-29
AU2004303735A1 (en)	2005-07-07
IL175958A0 (en)	2006-10-05
CN1918160A (zh)	2007-02-21
EP1699791A1 (en)	2006-09-13
TW200604197A (en)	2006-02-01
US7524856B2 (en)	2009-04-28
AR046992A1 (es)	2006-01-04
NO20063355L (no)	2006-09-22
AU2004303735B2 (en)	2007-09-20
BRPI0417036A (pt)	2007-02-06
MXPA06007025A (es)	2006-08-31
SE0303541D0 (sv)	2003-12-22
KR20060117343A (ko)	2006-11-16
US20090298861A1 (en)	2009-12-03
CA2548494A1 (en)	2005-07-07
JP2007515476A (ja)	2007-06-14
WO2005061499A1 (en)	2005-07-07
US20070099945A1 (en)	2007-05-03

Publication	Publication Date	Title
ZA200605082B (en)	2007-11-28	Novel tricyclic spiroderivatives as modulators of chemokine receptor activity
RU2481332C2 (ru)	2013-05-10	Октагидропенталеновые соединения в качестве антагонистов хемокиновых рецепторов
KR101762981B1 (ko)	2017-07-28	기분 장해 치료제
JP2010510224A (ja)	2010-04-02	ケモカイン受容体拮抗薬としてのアミノピロリジン類
Maury et al.	1990	Correlation of serum cytokine levels with haematological abnormalities in human immunodeficiency virus infection
JPWO2005023771A1 (ja)	2006-11-02	ケモカインレセプターアンタゴニストおよびその医薬用途
CA2629777A1 (en)	2007-05-31	Spirocyclic compounds as hdac inhibitors
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