TW200815347A - Inhibitors of soluble adenylate cyclase - Google Patents

Inhibitors of soluble adenylate cyclase Download PDF

Info

Publication number: TW200815347A
Authority: TW; Taiwan
Prior art keywords: alkyl; group; cvc6; aryl; fluorenyl
Prior art date: 2006-03-23

Application number

TW096110185A

Other languages

English (en)

Chinese (zh)

Inventor

Bernd Buchmann

Dirk Kosemund

Bernd Menzenbach

Martin Fritsch

Original Assignee

Bayer Schering Pharma Ag

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.)

2006-03-23

Filing date

2007-03-23

Publication date

2008-04-01

2007-03-23 Application filed by Bayer Schering Pharma Ag filed Critical Bayer Schering Pharma Ag

2008-04-01 Publication of TW200815347A publication Critical patent/TW200815347A/zh

Links

108060000200 adenylate cyclase Proteins 0.000 title claims description 16
102000030621 adenylate cyclase Human genes 0.000 title claims description 16
239000003112 inhibitor Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 64
125000000217 alkyl group Chemical group 0.000 claims description 178
-1 hydroxy, methoxy, ethoxy, isopropoxy Chemical group 0.000 claims description 68
125000003118 aryl group Chemical group 0.000 claims description 64
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 63
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 53
125000004093 cyano group Chemical group *C#N 0.000 claims description 50
125000003545 alkoxy group Chemical group 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 33
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 29
239000000126 substance Substances 0.000 claims description 26
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
125000001072 heteroaryl group Chemical group 0.000 claims description 20
238000000034 method Methods 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
239000011737 fluorine Substances 0.000 claims description 16
229910052731 fluorine Inorganic materials 0.000 claims description 16
239000007789 gas Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 12
125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
239000008177 pharmaceutical agent Substances 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 7
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
229940124530 sulfonamide Drugs 0.000 claims description 6
150000003456 sulfonamides Chemical class 0.000 claims description 6
150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
239000002689 soil Substances 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
125000002252 acyl group Chemical group 0.000 claims 1
229940037003 alum Drugs 0.000 claims 1
229910052786 argon Inorganic materials 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
238000013329 compounding Methods 0.000 claims 1
210000004268 dentin Anatomy 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
238000009830 intercalation Methods 0.000 claims 1
210000000936 intestine Anatomy 0.000 claims 1
230000002175 menstrual effect Effects 0.000 claims 1
230000004060 metabolic process Effects 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
125000004964 sulfoalkyl group Chemical group 0.000 claims 1
229910052727 yttrium Inorganic materials 0.000 claims 1
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 4
229940079593 drug Drugs 0.000 abstract 1
239000000243 solution Substances 0.000 description 29
101710205046 Adenylate cyclase type 10 Proteins 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000012360 testing method Methods 0.000 description 20
230000000694 effects Effects 0.000 description 19
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
239000002585 base Substances 0.000 description 17
230000008010 sperm capacitation Effects 0.000 description 17
230000030120 acrosome reaction Effects 0.000 description 14
239000000203 mixture Substances 0.000 description 13
150000003573 thiols Chemical class 0.000 description 13
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
150000001412 amines Chemical class 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
229910001868 water Inorganic materials 0.000 description 11
102000004190 Enzymes Human genes 0.000 description 10
108090000790 Enzymes Proteins 0.000 description 10
GTSMOYLSFUBTMV-UHFFFAOYSA-N ethidium homodimer Chemical compound [H+].[H+].[Cl-].[Cl-].[Cl-].[Cl-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2C(C)=[N+]1CCCNCCNCCC[N+](C1=CC(N)=CC=C1C1=CC=C(N)C=C11)=C1C1=CC=CC=C1 GTSMOYLSFUBTMV-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002555 ionophore Substances 0.000 description 8
230000000236 ionophoric effect Effects 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000002953 phosphate buffered saline Substances 0.000 description 7
238000010186 staining Methods 0.000 description 7
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 6
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 6
101710095468 Cyclase Proteins 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
210000001550 testis Anatomy 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
238000002866 fluorescence resonance energy transfer Methods 0.000 description 5
238000005259 measurement Methods 0.000 description 5
239000012528 membrane Substances 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
239000000523 sample Substances 0.000 description 5
210000000582 semen Anatomy 0.000 description 5
239000000725 suspension Substances 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001514 detection method Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229940011871 estrogen Drugs 0.000 description 4
239000000262 estrogen Substances 0.000 description 4
208000000509 infertility Diseases 0.000 description 4
230000036512 infertility Effects 0.000 description 4
150000002923 oximes Chemical class 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
230000008569 process Effects 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
210000004340 zona pellucida Anatomy 0.000 description 4
150000004057 1,4-benzoquinones Chemical class 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
101000775498 Homo sapiens Adenylate cyclase type 10 Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
102000001708 Protein Isoforms Human genes 0.000 description 3
108010029485 Protein Isoforms Proteins 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000027455 binding Effects 0.000 description 3
230000004663 cell proliferation Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
238000000684 flow cytometry Methods 0.000 description 3
MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 3
231100000535 infertility Toxicity 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
108020004999 messenger RNA Proteins 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
210000000287 oocyte Anatomy 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
239000008188 pellet Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
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239000002126 C01EB10 - Adenosine Substances 0.000 description 2
OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 2
239000007821 HATU Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
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241001465754 Metazoa Species 0.000 description 2
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239000007864 aqueous solution Substances 0.000 description 2
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238000004364 calculation method Methods 0.000 description 2
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239000003153 chemical reaction reagent Substances 0.000 description 2
239000003433 contraceptive agent Substances 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
125000006612 decyloxy group Chemical group 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
235000011180 diphosphates Nutrition 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 2
230000005284 excitation Effects 0.000 description 2
230000035558 fertility Effects 0.000 description 2
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229930182480 glucuronide Natural products 0.000 description 2
150000008134 glucuronides Chemical class 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
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HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
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150000003904 phospholipids Chemical class 0.000 description 1
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230000003449 preventive effect Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000047 product Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
230000003236 psychic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000003259 recombinant expression Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940043230 sarcosine Drugs 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
229940054269 sodium pyruvate Drugs 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
210000001082 somatic cell Anatomy 0.000 description 1
230000019100 sperm motility Effects 0.000 description 1
210000003802 sputum Anatomy 0.000 description 1
208000024794 sputum Diseases 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000000130 stem cell Anatomy 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
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230000000638 stimulation Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
229940034107 sulfazine Drugs 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
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125000001544 thienyl group Chemical group 0.000 description 1
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210000001519 tissue Anatomy 0.000 description 1
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ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
210000005239 tubule Anatomy 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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210000001534 vitelline membrane Anatomy 0.000 description 1
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238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

TW096110185A 2006-03-23 2007-03-23 Inhibitors of soluble adenylate cyclase TW200815347A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE102006014320A DE102006014320B4 (de)	2006-03-23	2006-03-23	Inhibitoren der löslichen Adenylatzklase

Publications (1)

Publication Number	Publication Date
TW200815347A true TW200815347A (en)	2008-04-01

Family

ID=38229991

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW096110185A TW200815347A (en)	2006-03-23	2007-03-23	Inhibitors of soluble adenylate cyclase

Country Status (12)

Country	Link
EP (1)	EP2001847A2 (fr)
JP (1)	JP2009531319A (fr)
KR (1)	KR20090007351A (fr)
CN (1)	CN101448789A (fr)
AR (1)	AR063661A1 (fr)
CA (1)	CA2646650A1 (fr)
DE (1)	DE102006014320B4 (fr)
DO (1)	DOP2007000059A (fr)
PE (1)	PE20080012A1 (fr)
TW (1)	TW200815347A (fr)
UY (1)	UY30236A1 (fr)
WO (1)	WO2007107385A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2036906A1 (fr) *	2007-09-05	2009-03-18	Bayer Schering Pharma Aktiengesellschaft	Azaindoles en tant qu'inhibiteurs d'adénylatcyclase soluble
CN108096244B (zh) *	2018-01-25	2020-11-24	昆明医科大学	1-氢-2-吲哚酮-3-苄基/取代苄基-3-甲酸酯类化合物的用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7442805B2 (en) *	2003-09-25	2008-10-28	Wyeth	Substituted sulfonamide-indoles
US7569604B2 (en) *	2004-06-22	2009-08-04	Vertex Pharmaceuticals Incorporated	Heterocyclic derivatives for modulation of calcium channels
DE102004047272A1 (de) *	2004-09-24	2006-04-06	Schering Ag	Inhibitoren der löslichen Adenylatzyklase

2006
- 2006-03-23 DE DE102006014320A patent/DE102006014320B4/de not_active Expired - Fee Related
2007
- 2007-03-22 CN CNA2007800187317A patent/CN101448789A/zh active Pending
- 2007-03-22 JP JP2009500787A patent/JP2009531319A/ja active Pending
- 2007-03-22 CA CA002646650A patent/CA2646650A1/fr not_active Abandoned
- 2007-03-22 KR KR1020087025818A patent/KR20090007351A/ko not_active Withdrawn
- 2007-03-22 WO PCT/EP2007/002708 patent/WO2007107385A2/fr not_active Ceased
- 2007-03-22 EP EP07723654A patent/EP2001847A2/fr not_active Withdrawn
- 2007-03-23 AR ARP070101194A patent/AR063661A1/es unknown
- 2007-03-23 PE PE2007000335A patent/PE20080012A1/es not_active Application Discontinuation
- 2007-03-23 UY UY30236A patent/UY30236A1/es not_active Application Discontinuation
- 2007-03-23 TW TW096110185A patent/TW200815347A/zh unknown
- 2007-03-23 DO DO2007000059A patent/DOP2007000059A/es unknown

Also Published As

Publication number	Publication date
JP2009531319A (ja)	2009-09-03
WO2007107385A2 (fr)	2007-09-27
DE102006014320A1 (de)	2007-09-27
DOP2007000059A (es)	2007-09-30
CN101448789A (zh)	2009-06-03
UY30236A1 (es)	2007-10-31
PE20080012A1 (es)	2008-04-03
DE102006014320B4 (de)	2009-01-22
CA2646650A1 (fr)	2007-09-27
WO2007107385A3 (fr)	2007-11-29
KR20090007351A (ko)	2009-01-16
AR063661A1 (es)	2009-02-11
EP2001847A2 (fr)	2008-12-17

Publication	Publication Date	Title
EP0929520B1 (fr)	2005-11-02	Banques combinatoires d'indolinone, produits et procedes associes pour traiter des maladies
EP1776340B1 (fr)	2008-12-03	Derives de n-(1 h-indolyl)-i h-ind0le-2-carb0xamides, leur preparation et leur application en therapeutique
US7449459B2 (en)	2008-11-11	Inhibitors of soluble adenylate cyclase
US20030144339A1 (en)	2003-07-31	Indole derivatives as mcp-1 receptor antagonists
US20070259872A1 (en)	2007-11-08	Inhibitors of soluble adenylate cyclase
US7417066B2 (en)	2008-08-26	Inhibitors of soluble adenylate cyclase
EP1888058B1 (fr)	2009-05-20	Inhibiteurs de l'adenylate cyclase soluble
CN101448789A (zh)	2009-06-03	可溶性腺苷酸环化酶抑制剂
US20090098189A1 (en)	2009-04-16	Azaindoles as inhibitors of soluble adenylate cyclase
US20070225284A1 (en)	2007-09-27	Inhibitors of soluble adenylate cyclase
JP2008514572A (ja)	2008-05-08	可溶性アデニル酸シクラーゼのインヒビターとしてのインドール誘導体
HK1118485A (en)	2009-02-13	Inhibitors of soluble adenylate cyclase