UA78021C2 - Thiazolidine carboxamide derivatives as modulators of prostaglandine f receptors - Google Patents

Thiazolidine carboxamide derivatives as modulators of prostaglandine f receptors Download PDF

Info

Publication number: UA78021C2
Authority: UA; Ukraine
Prior art keywords: thiazolidine; carboxamide; biphenyl; ylsulfonyl; phenylpropyl
Prior art date: 2002-03-28

Application number

UA20040907830A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Applied Research Systems

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.)

2002-03-28

Filing date

2003-03-27

Publication date

2007-02-15

2003-03-27 Application filed by Applied Research Systems filed Critical Applied Research Systems

2007-02-15 Publication of UA78021C2 publication Critical patent/UA78021C2/uk

Links

YDGXLVKDGGLWPF-UHFFFAOYSA-N 1,3-thiazolidine-2-carboxamide Chemical class NC(=O)C1NCCS1 YDGXLVKDGGLWPF-UHFFFAOYSA-N 0.000 title claims abstract description 45
-1 heterocycloalkyi Chemical group 0.000 claims abstract description 154
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 79
125000003118 aryl group Chemical group 0.000 claims abstract description 74
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 64
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
208000005107 Premature Birth Diseases 0.000 claims abstract description 14
238000011282 treatment Methods 0.000 claims abstract description 13
206010036590 Premature baby Diseases 0.000 claims abstract description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
125000002252 acyl group Chemical group 0.000 claims abstract description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
125000005842 heteroatom Chemical group 0.000 claims abstract description 8
208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 7
206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 259
238000000034 method Methods 0.000 claims description 154
239000004305 biphenyl Substances 0.000 claims description 130
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 69
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 37
102000015433 Prostaglandin Receptors Human genes 0.000 claims description 24
108010050183 Prostaglandin Receptors Proteins 0.000 claims description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 22
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 14
235000010290 biphenyl Nutrition 0.000 claims description 11
210000003754 fetus Anatomy 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
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 9
229910052796 boron Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 9
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004442 acylamino group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
230000002028 premature Effects 0.000 claims description 6
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
229940126601 medicinal product Drugs 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 claims description 2
125000000539 amino acid group Chemical group 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000000945 filler Substances 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims 2
OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical class C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 claims 1
125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
101150104606 pgl gene Proteins 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
150000003457 sulfones Chemical class 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 21
208000006399 Premature Obstetric Labor Diseases 0.000 abstract description 6
125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
125000006715 (C1-C5) alkylthio group Chemical group 0.000 abstract 1
125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
238000011321 prophylaxis Methods 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 149
239000000243 solution Substances 0.000 description 95
239000000203 mixture Substances 0.000 description 86
239000007858 starting material Substances 0.000 description 79
238000005481 NMR spectroscopy Methods 0.000 description 75
239000011541 reaction mixture Substances 0.000 description 74
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
239000000047 product Substances 0.000 description 60
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
150000001412 amines Chemical class 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 43
150000003180 prostaglandins Chemical class 0.000 description 42
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
239000002904 solvent Substances 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
210000004027 cell Anatomy 0.000 description 32
238000007429 general method Methods 0.000 description 32
239000007787 solid Substances 0.000 description 32
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
238000003786 synthesis reaction Methods 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
230000015572 biosynthetic process Effects 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
102000005962 receptors Human genes 0.000 description 25
108020003175 receptors Proteins 0.000 description 25
235000019439 ethyl acetate Nutrition 0.000 description 24
239000012044 organic layer Substances 0.000 description 24
230000000694 effects Effects 0.000 description 23
210000004291 uterus Anatomy 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
238000012360 testing method Methods 0.000 description 22
238000002360 preparation method Methods 0.000 description 21
239000012043 crude product Substances 0.000 description 20
239000011347 resin Substances 0.000 description 19
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229920006395 saturated elastomer Polymers 0.000 description 18
238000010532 solid phase synthesis reaction Methods 0.000 description 18
LNOLJFCCYQZFBQ-BUHFOSPRSA-N (ne)-n-[(4-nitrophenyl)-phenylmethylidene]hydroxylamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=N/O)/C1=CC=CC=C1 LNOLJFCCYQZFBQ-BUHFOSPRSA-N 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
229940125782 compound 2 Drugs 0.000 description 16
239000003921 oil Substances 0.000 description 16
235000019198 oils Nutrition 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
HYAXPNDMEODKHI-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-thiazolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCSC1C(O)=O HYAXPNDMEODKHI-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
229940094443 oxytocics prostaglandins Drugs 0.000 description 15
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
238000000746 purification Methods 0.000 description 14
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 14
239000000725 suspension Substances 0.000 description 14
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 13
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 13
101800000989 Oxytocin Proteins 0.000 description 13
102100031951 Oxytocin-neurophysin 1 Human genes 0.000 description 13
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XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 13
229960001723 oxytocin Drugs 0.000 description 13
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150000003141 primary amines Chemical class 0.000 description 13
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 12
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 12
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208000036029 Uterine contractions during pregnancy Diseases 0.000 description 10
239000008346 aqueous phase Substances 0.000 description 10
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WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 10
150000002923 oximes Chemical class 0.000 description 10
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
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OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 8
ALBQXDHCMLLQMB-UHFFFAOYSA-N 4-phenylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1=CC=CC=C1 ALBQXDHCMLLQMB-UHFFFAOYSA-N 0.000 description 8
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 7
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Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
- 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
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
- 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
- A61P15/06—Antiabortive agents; Labour repressants
- 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
- 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
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- 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
- C07D417/14—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 three or more hetero rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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UA20040907830A 2002-03-28 2003-03-27 Thiazolidine carboxamide derivatives as modulators of prostaglandine f receptors UA78021C2 (en)

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Application Number	Priority Date	Filing Date	Title
EP02100314		2002-03-28
PCT/EP2003/050083 WO2003082278A1 (en)	2002-03-28	2003-03-27	Thiazolidine carboxamide derivatives as modulators of the prostaglandin f receptor

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UA20040907830A UA78021C2 (en)	2002-03-28	2003-03-27	Thiazolidine carboxamide derivatives as modulators of prostaglandine f receptors

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US (2)	US20050215605A1 (sr)
EP (1)	EP1487442B1 (sr)
JP (1)	JP4602672B2 (sr)
KR (1)	KR20040095311A (sr)
CN (1)	CN100484524C (sr)
AT (1)	ATE489951T1 (sr)
AU (2)	AU2003240757B2 (sr)
BR (1)	BR0308748A (sr)
CA (1)	CA2477265A1 (sr)
DE (1)	DE60335175D1 (sr)
EA (1)	EA007328B1 (sr)
ES (1)	ES2360882T3 (sr)
HR (1)	HRP20040759A2 (sr)
IL (1)	IL164212A0 (sr)
MX (1)	MXPA04009374A (sr)
NO (1)	NO20044262L (sr)
PL (1)	PL372919A1 (sr)
RS (1)	RS81604A (sr)
UA (1)	UA78021C2 (sr)
WO (1)	WO2003082278A1 (sr)
ZA (1)	ZA200406763B (sr)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20040095311A (ko) *	2002-03-28	2004-11-12	어플라이드 리서치 시스템스 에이알에스 홀딩 엔.브이.	프로스타글란딘 ｆ 수용체의 모듈레이터로서의 티아졸리딘카르복사미드 유도체
CA2511970C (en)	2003-01-14	2012-06-26	Cytokinetics, Inc.	Urea derivatives useful in the treatment of heart failure
MY150129A (en)	2004-04-09	2013-11-29	Archer Daniels Midland Co	Method of preparing fatty acid alkyl esters from waste or recycled fatty acid stock
JP5080970B2 (ja)	2004-06-17	2012-11-21	サイトキネティクス・インコーポレーテッド	心疾患を治療するための置換尿素誘導体
US7176222B2 (en)	2004-07-27	2007-02-13	Cytokinetics, Inc.	Syntheses of ureas
TW200808321A (en)	2005-12-15	2008-02-16	Cytokinetics Inc	Certain chemical entities, compositions and methods
US7825120B2 (en)	2005-12-15	2010-11-02	Cytokinetics, Inc.	Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas
EP1959962A2 (en)	2005-12-16	2008-08-27	Cytokinetics, Inc.	Certain chemical entities, compositions, and methods
EP1962852B1 (en)	2005-12-19	2017-01-25	Cytokinetics, Inc.	Compounds, compositions and methods
KR101437302B1 (ko) *	2006-02-07	2014-09-02	가부시키가이샤 아루떼꾸 우에노	프로스타글란딘 유도체의 제조 방법
US20090163586A1 (en)	2007-12-20	2009-06-25	Astrazeneca Ab	Bis-(Sulfonylamino) Derivatives in Therapy 205
WO2011014649A1 (en)	2009-07-29	2011-02-03	Duke University	Compositions and methods for inhibiting hair growth
US8710043B2 (en)	2011-06-24	2014-04-29	Amgen Inc.	TRPM8 antagonists and their use in treatments
EP2723718A1 (en)	2011-06-24	2014-04-30	Amgen Inc.	Trpm8 antagonists and their use in treatments
US8952009B2 (en)	2012-08-06	2015-02-10	Amgen Inc.	Chroman derivatives as TRPM8 inhibitors
US20160264536A1 (en)	2013-10-23	2016-09-15	Takeda Pharmaceutical Company Limited	Heterocyclic compound
CN109790133A (zh)	2016-01-04	2019-05-21	奥布赛瓦股份公司	羟丙基噻唑烷羧酰胺衍生物的α-氨基酯及其盐形式、晶体多形体
US9447055B1 (en)	2016-01-04	2016-09-20	Merck Serono S.A.	α-amino esters of hydroxypropylthiazolidine carboxamide derivative and salt form, crystal polymorph thereof
JP6933322B2 (ja) *	2016-01-04	2021-09-08	メルクセローノエス．エー．	ヒドロキシプロピルチアゾリジンカルボキサミド誘導体のｌ−バリネート及びその塩形態、結晶多形
EA039545B1 (ru) *	2016-10-13	2022-02-09	Обсева С.А.	Способы предотвращения преждевременных родов с помощью комбинации ингибитора pgf2 и токолитического агента
WO2018113785A1 (zh) *	2016-12-22	2018-06-28	广州华睿光电材料有限公司	含呋喃交联基团的聚合物及其应用
US11534428B1 (en)	2018-05-16	2022-12-27	Xoma (Us) Llc	Compositions and methods for delaying the incidence of labor
US20240024294A1 (en)	2020-11-16	2024-01-25	Xoma (Us) Llc	Compositions and methods for the treatment or prevention of preterm labor
CA3204921A1 (en) *	2020-12-11	2022-06-16	Elise A. Olsen	Compositions and methods for inhibiting hair growth
WO2025124698A1 (en)	2023-12-12	2025-06-19	Idorsia Pharmaceuticals Ltd	Aryl sulfone and sulfanone derivatives as orexin receptor modulators
TW202542165A (zh)	2023-12-19	2025-11-01	瑞士商愛杜西亞製藥有限公司	大環食慾素激動劑

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4016270A (en) *	1975-10-31	1977-04-05	Alza Corporation	Method for treating dysmenorrhea with a uterine therapeutic system
JPH0662529B2 (ja) *	1984-07-13	1994-08-17	三共株式会社	アミノ酸誘導体
JPS6450818A (en) *	1987-08-20	1989-02-27	Tsumura & Co	Prostaglandin f2alpha-inhibitor
US5338755A (en) *	1990-07-31	1994-08-16	Elf Sanofi	N-sulfonylindoline derivatives, their preparation and the pharmaceutical compositions in which they are present
US6271201B1 (en)	1993-07-15	2001-08-07	Board Of Regents, The University Of Texas System	Methods for the selective regulation of placental prostanoids and inhibition of labor using IGF-I
JP3347330B2 (ja) *	1996-08-28	2002-11-20	ザプロクターアンドギャンブルカンパニー	１，３―ジヘテロ環式メタロプロテアーゼ阻害剤類
AR016133A1 (es) *	1997-07-31	2001-06-20	Wyeth Corp	Compuesto de carbamiloxi que inhiben la adhesion de leucocitos mediada por vla-4, compuestos que son prodrogas de dichos compuestos, composicionfarmaceutica, metodo para fijar vla-4 a una muestra biologica, metodo para el tratamiento de una condicion inflamatoria
JP2001512138A (ja) *	1997-07-31	2001-08-21	エラン・ファーマシューティカルズ・インコーポレーテッド	Ｖｌａ−４が介在する白血球付着を阻害するベンジル化合物
US6645939B1 (en) *	1997-11-24	2003-11-11	Merck & Co., Inc.	Substituted β-alanine derivatives as cell adhesion inhibitors
KR20040095311A (ko)	2002-03-28	2004-11-12	어플라이드 리서치 시스템스 에이알에스 홀딩 엔.브이.	프로스타글란딘 ｆ 수용체의 모듈레이터로서의 티아졸리딘카르복사미드 유도체

2003
- 2003-03-27 KR KR10-2004-7015040A patent/KR20040095311A/ko not_active Ceased
- 2003-03-27 RS YU81604A patent/RS81604A/sr unknown
- 2003-03-27 UA UA20040907830A patent/UA78021C2/uk unknown
- 2003-03-27 IL IL16421203A patent/IL164212A0/xx unknown
- 2003-03-27 CA CA002477265A patent/CA2477265A1/en not_active Abandoned
- 2003-03-27 US US10/508,014 patent/US20050215605A1/en not_active Abandoned
- 2003-03-27 JP JP2003579816A patent/JP4602672B2/ja not_active Expired - Lifetime
- 2003-03-27 AU AU2003240757A patent/AU2003240757B2/en not_active Ceased
- 2003-03-27 MX MXPA04009374A patent/MXPA04009374A/es active IP Right Grant
- 2003-03-27 WO PCT/EP2003/050083 patent/WO2003082278A1/en not_active Ceased
- 2003-03-27 AT AT03730168T patent/ATE489951T1/de not_active IP Right Cessation
- 2003-03-27 HR HRP20040759 patent/HRP20040759A2/hr not_active Application Discontinuation
- 2003-03-27 PL PL03372919A patent/PL372919A1/xx not_active Application Discontinuation
- 2003-03-27 EA EA200401270A patent/EA007328B1/ru unknown
- 2003-03-27 DE DE60335175T patent/DE60335175D1/de not_active Expired - Lifetime
- 2003-03-27 CN CNB038115603A patent/CN100484524C/zh not_active Expired - Lifetime
- 2003-03-27 BR BR0308748-4A patent/BR0308748A/pt not_active IP Right Cessation
- 2003-03-27 ES ES03730168T patent/ES2360882T3/es not_active Expired - Lifetime
- 2003-03-27 ZA ZA200406763A patent/ZA200406763B/en unknown
- 2003-03-27 EP EP03730168A patent/EP1487442B1/en not_active Expired - Lifetime
2004
- 2004-10-07 NO NO20044262A patent/NO20044262L/no not_active Application Discontinuation
2008
- 2008-06-17 US US12/140,682 patent/US8415480B2/en not_active Expired - Lifetime
- 2008-08-19 AU AU2008207407A patent/AU2008207407A1/en not_active Abandoned

Also Published As

Publication number	Publication date
US20080255094A1 (en)	2008-10-16
JP4602672B2 (ja)	2010-12-22
ATE489951T1 (de)	2010-12-15
EA200401270A1 (ru)	2005-02-24
US20050215605A1 (en)	2005-09-29
DE60335175D1 (de)	2011-01-13
NO20044262L (no)	2004-10-07
US8415480B2 (en)	2013-04-09
EP1487442B1 (en)	2010-12-01
PL372919A1 (en)	2005-08-08
EP1487442A1 (en)	2004-12-22
ES2360882T3 (es)	2011-06-10
AU2003240757A1 (en)	2003-10-13
RS81604A (sr)	2006-12-15
IL164212A0 (en)	2005-12-18
BR0308748A (pt)	2005-01-11
AU2003240757B2 (en)	2008-07-03
EA007328B1 (ru)	2006-08-25
US20090215749A9 (en)	2009-08-27
ZA200406763B (en)	2005-09-30
WO2003082278A1 (en)	2003-10-09
MXPA04009374A (es)	2005-01-25
CN1655780A (zh)	2005-08-17
CA2477265A1 (en)	2003-10-09
HK1075215A1 (zh)	2005-12-09
KR20040095311A (ko)	2004-11-12
CN100484524C (zh)	2009-05-06
HRP20040759A2 (en)	2004-12-31
JP2005531524A (ja)	2005-10-20
AU2008207407A1 (en)	2008-09-11

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