CA2359562A1 - Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents - Google Patents
Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents Download PDFInfo
- Publication number
- CA2359562A1 CA2359562A1 CA002359562A CA2359562A CA2359562A1 CA 2359562 A1 CA2359562 A1 CA 2359562A1 CA 002359562 A CA002359562 A CA 002359562A CA 2359562 A CA2359562 A CA 2359562A CA 2359562 A1 CA2359562 A1 CA 2359562A1
- Authority
- CA
- Canada
- Prior art keywords
- carbons
- methyl
- alkyl
- nitrophenylimino
- thiazolidine
- Prior art date
- 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.)
- Abandoned
Links
- 102000003998 progesterone receptors Human genes 0.000 title abstract description 11
- 108090000468 progesterone receptors Proteins 0.000 title abstract description 11
- 239000000203 mixture Substances 0.000 title description 128
- 239000011230 binding agent Substances 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 1063
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
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- 230000015572 biosynthetic process Effects 0.000 claims description 147
- 125000001424 substituent group Chemical group 0.000 claims description 122
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- -1 C(O)N(R6)(R7) Chemical group 0.000 claims description 98
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 150000002367 halogens Chemical class 0.000 claims description 83
- 238000011282 treatment Methods 0.000 claims description 70
- 229910052760 oxygen Inorganic materials 0.000 claims description 55
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 229910052717 sulfur Inorganic materials 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical group C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- FSKNZNKSZYBXPI-UHFFFAOYSA-N 4-[(1-cyclopentyl-3-thia-1-azaspiro[4.4]nonan-2-ylidene)amino]-3-ethylbenzonitrile Chemical compound CCC1=CC(C#N)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 FSKNZNKSZYBXPI-UHFFFAOYSA-N 0.000 claims description 10
- SKACZZQWCFGTOO-UHFFFAOYSA-N 1-cyclopentyl-n-(2-methyl-4-nitrophenyl)-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 SKACZZQWCFGTOO-UHFFFAOYSA-N 0.000 claims description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
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- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
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- UOBAUMNLOZCUIS-UHFFFAOYSA-N 2-(2-methyl-4-nitrophenyl)imino-3-(2-methylpropyl)-1,3-thiazolidin-4-one Chemical compound CC(C)CN1C(=O)CSC1=NC1=CC=C([N+]([O-])=O)C=C1C UOBAUMNLOZCUIS-UHFFFAOYSA-N 0.000 claims description 4
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- ZXIOHKLKWRDUKK-UHFFFAOYSA-N 1-cyclopentyl-n-(2,3-dimethyl-4-nitrophenyl)-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound CC1=C(C)C([N+]([O-])=O)=CC=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 ZXIOHKLKWRDUKK-UHFFFAOYSA-N 0.000 claims description 3
- PTZJSANBUKXPHQ-UHFFFAOYSA-N 4-[(1-cyclopentyl-3-thia-1-azaspiro[4.4]nonan-2-ylidene)amino]-2,3-dimethylbenzonitrile Chemical compound C1=CC(C#N)=C(C)C(C)=C1N=C1N(C2CCCC2)C2(CCCC2)CS1 PTZJSANBUKXPHQ-UHFFFAOYSA-N 0.000 claims description 3
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- LAUYJPDPFRHBEN-UHFFFAOYSA-N 1-cyclopentyl-n-(3-methyl-4-nitrophenyl)-3-thia-1-azaspiro[4.4]nonan-2-imine Chemical compound C1=C([N+]([O-])=O)C(C)=CC(N=C2N(C3(CCCC3)CS2)C2CCCC2)=C1 LAUYJPDPFRHBEN-UHFFFAOYSA-N 0.000 claims description 2
- FQZUPLVJTIZVCM-UHFFFAOYSA-N 2,3-dimethyl-4-[[1-(2-methylpropyl)-3-thia-1-azaspiro[4.4]nonan-2-ylidene]amino]benzonitrile Chemical compound CC(C)CN1C(=NC=2C(=C(C)C(C#N)=CC=2)C)SCC11CCCC1 FQZUPLVJTIZVCM-UHFFFAOYSA-N 0.000 claims description 2
- HFPKXEQJCQBPIP-UHFFFAOYSA-N 2-(3-methyl-4-nitrophenyl)imino-3-(2-methylpropyl)-1,3-thiazolidin-4-one Chemical compound CC(C)CN1C(=O)CSC1=NC1=CC=C([N+]([O-])=O)C(C)=C1 HFPKXEQJCQBPIP-UHFFFAOYSA-N 0.000 claims description 2
- NTUNKNYPEADWOY-UHFFFAOYSA-N 3-(1-cyclohexylethyl)-2-(2-methyl-4-nitrophenyl)imino-1,3-thiazolidin-4-one Chemical compound O=C1CSC(=NC=2C(=CC(=CC=2)[N+]([O-])=O)C)N1C(C)C1CCCCC1 NTUNKNYPEADWOY-UHFFFAOYSA-N 0.000 claims description 2
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- 238000002953 preparative HPLC Methods 0.000 description 1
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
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- XWJPHVIFPQWASO-UHFFFAOYSA-N s-[[1-(cyclopentylamino)cyclopentyl]methyl] ethanethioate Chemical compound C1CCCC1NC1(CSC(=O)C)CCCC1 XWJPHVIFPQWASO-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
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- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
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- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 1
- YDAXJFVVHZUVMU-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)-n-(2-methylprop-2-enyl)carbamate Chemical compound CC(=C)CN(CCO)C(=O)OC(C)(C)C YDAXJFVVHZUVMU-UHFFFAOYSA-N 0.000 description 1
- HYEXCBXDBHHJJY-SECBINFHSA-N tert-butyl n-[(3r)-1-hydroxy-4-methylpentan-3-yl]carbamate Chemical compound OCC[C@H](C(C)C)NC(=O)OC(C)(C)C HYEXCBXDBHHJJY-SECBINFHSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
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- 238000012800 visualization Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
- C07D277/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23190699A | 1999-01-14 | 1999-01-14 | |
| US09/231,906 | 1999-01-14 | ||
| PCT/US1999/029601 WO2000042031A2 (en) | 1999-01-14 | 1999-12-14 | Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2359562A1 true CA2359562A1 (en) | 2000-07-20 |
Family
ID=22871101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002359562A Abandoned CA2359562A1 (en) | 1999-01-14 | 1999-12-14 | Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1144396A2 (cs) |
| JP (1) | JP2002534517A (cs) |
| KR (1) | KR20010089831A (cs) |
| CN (1) | CN1337955A (cs) |
| AR (1) | AR022214A1 (cs) |
| AU (1) | AU2708700A (cs) |
| BG (1) | BG105761A (cs) |
| BR (1) | BR9916999A (cs) |
| CA (1) | CA2359562A1 (cs) |
| CO (1) | CO5160338A1 (cs) |
| CZ (1) | CZ20012530A3 (cs) |
| GT (1) | GT200000003A (cs) |
| HU (1) | HUP0105134A2 (cs) |
| ID (1) | ID30514A (cs) |
| IL (1) | IL144031A0 (cs) |
| NO (1) | NO20013318L (cs) |
| SK (1) | SK10032001A3 (cs) |
| SV (1) | SV2002000005A (cs) |
| TR (1) | TR200102041T2 (cs) |
| WO (1) | WO2000042031A2 (cs) |
| ZA (1) | ZA200105253B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8193252B1 (en) | 1999-08-31 | 2012-06-05 | Bayer Pharma AG | Mesoprogestins (progesterone receptor modulators) for the treatment and prevention of benign hormone dependent gynecological disorders |
| EA007854B1 (ru) * | 1999-08-31 | 2007-02-27 | Шеринг Акциенгезельшафт | Мезопрогестины (модуляторы рецептора прогестерона) в качестве средств лечения и предупреждения доброкачественных зависящих от гормонов гинекологических нарушений |
| HUP0202460A3 (en) * | 1999-08-31 | 2004-04-28 | Schering Ag | Mesoprogestins (progesterone receptor modulators) as a component of compositions for hormone replacement therapy (hrt) |
| ATE393150T1 (de) * | 1999-09-14 | 2008-05-15 | Shionogi & Co | 2-imino-1,3-thiazin-derivate |
| JPWO2001072723A1 (ja) * | 2000-03-28 | 2004-01-08 | 日本曹達株式会社 | オキサ(チア)ゾリジン誘導体および抗炎症薬 |
| EP1317456A2 (en) * | 2000-09-07 | 2003-06-11 | Bayer Corporation | Cyclic and acyclic amidines and pharmaceutical compositions containing them for use as progesterone receptor binding agents |
| CA2440186C (en) * | 2001-03-08 | 2009-01-13 | Shionogi & Co., Ltd. | Medicinal composition containing 1,3-thiazine derivative |
| US7189751B2 (en) | 2001-06-25 | 2007-03-13 | Nippon Soda Co., Ltd. | Oxa(thia)zolidine compounds, process for preparation thereof and anti-inflammatory agents |
| EP1465882B1 (en) | 2001-12-21 | 2011-08-24 | X-Ceptor Therapeutics, Inc. | Hetrocyclic modulators of nuclear receptors |
| US20060142387A1 (en) * | 2003-06-10 | 2006-06-29 | Rodolfo Cadilla | Chemical compounds |
| CN103382158B (zh) * | 2013-07-29 | 2015-11-18 | 张家港市大伟助剂有限公司 | 一种2-环戊基氨基乙醇的制备方法 |
| BR112022000188A2 (pt) * | 2019-07-10 | 2022-02-22 | Bayer Ag | Método para a preparação de 2-(fenilimino)-1,3-tiazolidin-4-onas |
| CN114507143A (zh) * | 2022-02-26 | 2022-05-17 | 江苏壹药新材料有限公司 | 一种2-乙基-1-氟-4-硝基苯的合成方法 |
| CN114671828B (zh) * | 2022-04-28 | 2024-05-31 | 蔚林新材料科技股份有限公司 | 一种3-甲基-2-噻唑硫酮的制备方法 |
| CN114957288B (zh) * | 2022-06-07 | 2024-02-13 | 苏州华道生物药业股份有限公司 | 一种盐酸四咪唑的合成方法 |
| CN115925559B (zh) * | 2022-11-11 | 2024-12-17 | 上海泰坦科技股份有限公司 | 一种1-氨基-1-环戊基甲醇的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670754A1 (de) * | 1966-09-27 | 1970-12-23 | Bayer Ag | Verfahren zur Herstellung von 2-Phenylimino-oxazolidinen |
| FR1510015A (fr) * | 1966-12-05 | 1968-01-19 | Aquitaine Petrole | Préparation d'imino-thiazolidines |
| DE1767335A1 (de) * | 1968-04-27 | 1971-09-02 | Bayer Ag | Anaesthetikum fuer Tiere |
| DE1963193A1 (de) * | 1969-12-17 | 1971-06-24 | Bayer Ag | N-substituierte 2-Arylimino-oxazolidine,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasiticide |
| FR2117337A5 (en) * | 1970-12-04 | 1972-07-21 | Eastman Kodak Co | Merocyanine dye sensitisers - contg basic and acidic gps for silver halide emulsions |
| US3787575A (en) * | 1970-12-17 | 1974-01-22 | Bayer Ag | N-substituted-2-arylimino-oxazolidines used as acaricides |
| GB1342232A (en) * | 1971-07-29 | 1974-01-03 | Bayer Ag | Aryliminothiazolidines a process for their preparation and their use as acaricides |
| CH614946A5 (cs) * | 1975-05-07 | 1979-12-28 | Ciba Geigy Ag | |
| DE2658138A1 (de) * | 1976-12-22 | 1978-07-06 | Bayer Ag | Substituierte 2-phenylimino-thiazolidine, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizide |
| DE2926771A1 (de) * | 1979-07-03 | 1981-01-15 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| DE3049460A1 (de) * | 1980-12-30 | 1982-07-29 | Hoechst Ag, 6000 Frankfurt | "thiazolinderivate, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| DE3505432A1 (de) * | 1985-02-16 | 1986-08-21 | Hoechst Ag, 6230 Frankfurt | Pflanzenschutz- und schaedlingsbekaempfungsmittel auf der basis von thiazolidinderivaten sowie neue thiazolidinderivate und verfahren zu ihrer herstellung |
| EP0265162B1 (en) * | 1986-10-17 | 1991-03-06 | Stauffer Chemical Company | Iminooxazolidines, process of preparation and method of use |
| US4806653A (en) * | 1986-10-17 | 1989-02-21 | Stauffer Chemical Company | Process for preparation of iminooxazolidines |
| EP0270138B1 (en) * | 1986-11-04 | 1991-05-29 | Duphar International Research B.V | Substituted 2-phenylimino-oxazolidine compounds having herbicidal activity |
| WO1989004595A2 (en) * | 1987-11-19 | 1989-06-01 | The Upjohn Company | Ectoparasiticides |
-
1999
- 1999-12-14 HU HU0105134A patent/HUP0105134A2/hu unknown
- 1999-12-14 BR BR9916999-1A patent/BR9916999A/pt not_active IP Right Cessation
- 1999-12-14 TR TR2001/02041T patent/TR200102041T2/xx unknown
- 1999-12-14 JP JP2000593599A patent/JP2002534517A/ja active Pending
- 1999-12-14 AU AU27087/00A patent/AU2708700A/en not_active Abandoned
- 1999-12-14 CN CN99816464A patent/CN1337955A/zh active Pending
- 1999-12-14 IL IL14403199A patent/IL144031A0/xx unknown
- 1999-12-14 KR KR1020017008891A patent/KR20010089831A/ko not_active Withdrawn
- 1999-12-14 WO PCT/US1999/029601 patent/WO2000042031A2/en not_active Ceased
- 1999-12-14 ID IDW00200101749A patent/ID30514A/id unknown
- 1999-12-14 CA CA002359562A patent/CA2359562A1/en not_active Abandoned
- 1999-12-14 EP EP99968883A patent/EP1144396A2/en not_active Withdrawn
- 1999-12-14 SK SK1003-2001A patent/SK10032001A3/sk unknown
- 1999-12-14 CZ CZ20012530A patent/CZ20012530A3/cs unknown
-
2000
- 2000-01-06 AR ARP000100044A patent/AR022214A1/es unknown
- 2000-01-13 GT GT200000003A patent/GT200000003A/es unknown
- 2000-01-13 CO CO00001518A patent/CO5160338A1/es unknown
- 2000-01-13 SV SV2000000005A patent/SV2002000005A/es unknown
-
2001
- 2001-06-26 ZA ZA200105253A patent/ZA200105253B/en unknown
- 2001-07-04 NO NO20013318A patent/NO20013318L/no not_active Application Discontinuation
- 2001-08-01 BG BG105761A patent/BG105761A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000042031A2 (en) | 2000-07-20 |
| WO2000042031A3 (en) | 2000-11-09 |
| SV2002000005A (es) | 2002-07-16 |
| TR200102041T2 (tr) | 2001-12-21 |
| EP1144396A2 (en) | 2001-10-17 |
| CN1337955A (zh) | 2002-02-27 |
| HUP0105134A2 (hu) | 2002-04-29 |
| CO5160338A1 (es) | 2002-05-30 |
| NO20013318D0 (no) | 2001-07-04 |
| IL144031A0 (en) | 2002-04-21 |
| KR20010089831A (ko) | 2001-10-08 |
| ZA200105253B (en) | 2002-09-05 |
| NO20013318L (no) | 2001-08-30 |
| AU2708700A (en) | 2000-08-01 |
| AR022214A1 (es) | 2002-09-04 |
| BR9916999A (pt) | 2001-10-30 |
| SK10032001A3 (sk) | 2002-05-09 |
| ID30514A (id) | 2001-12-13 |
| BG105761A (en) | 2002-03-29 |
| JP2002534517A (ja) | 2002-10-15 |
| CZ20012530A3 (cs) | 2002-02-13 |
| GT200000003A (es) | 2001-07-06 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |