ZA200300170B - Pyrrolidine derivatives as metalloprotease inhibitors. - Google Patents
Pyrrolidine derivatives as metalloprotease inhibitors. Download PDFInfo
- Publication number
- ZA200300170B ZA200300170B ZA200300170A ZA200300170A ZA200300170B ZA 200300170 B ZA200300170 B ZA 200300170B ZA 200300170 A ZA200300170 A ZA 200300170A ZA 200300170 A ZA200300170 A ZA 200300170A ZA 200300170 B ZA200300170 B ZA 200300170B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrrolidine
- mercapto
- carboxylic acid
- alkyl
- compounds according
- Prior art date
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- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 2
- 150000003235 pyrrolidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- -1 diarylalkyl Chemical group 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 14
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
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- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- 125000004001 thioalkyl group Chemical group 0.000 description 1
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C07D207/36—Oxygen or sulfur atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- 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
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- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Y02P20/50—Improvements relating to the production of bulk chemicals
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EP00114949 | 2000-07-19 |
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JP3983663B2 (ja) * | 2000-07-19 | 2007-09-26 | エフ.ホフマン−ラ ロシュ アーゲー | メタロプロテアーゼインヒビターとしてのピロリジン誘導体 |
US7405234B2 (en) * | 2002-05-17 | 2008-07-29 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
US7176201B2 (en) | 2002-10-07 | 2007-02-13 | The Regents Of The University Of California | Modulation of anxiety through blockade of anandamide hydrolysis |
US7388027B2 (en) * | 2004-03-04 | 2008-06-17 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
CN101376656A (zh) * | 2007-08-30 | 2009-03-04 | 山东轩竹医药科技有限公司 | 培南衍生物 |
EP2543368A1 (en) | 2007-12-11 | 2013-01-09 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
WO2010028051A2 (en) * | 2008-09-03 | 2010-03-11 | Florida State University Research Foundation, Inc. | Substituted heterocyclic mercaptosulfonamide metalloprotease inhibitors |
RU2022103033A (ru) | 2015-07-02 | 2022-04-01 | ХОРАЙЗОН ОРФАН ЭлЭлСи | Цистеаминдиоксигеназа-резистентные аналоги цистеамина и их применение |
EP3740466B1 (en) * | 2018-01-17 | 2024-03-06 | Migal Galilee Research Institute Ltd. | New methionine metabolic pathway inhibitors |
CN111825582B (zh) * | 2020-08-12 | 2022-04-08 | 江西理工大学 | 一种以芳基磺酰氯为硫源合成β-硫代羰基化合物的方法 |
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CA1281720C (en) * | 1984-11-08 | 1991-03-19 | Makoto Sunagawa | Carbapenem compounds and production thereof |
US4925838A (en) * | 1988-03-18 | 1990-05-15 | Fujisawa Pharmaceutical Company, Ltd. | 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds |
US5317016A (en) * | 1991-08-20 | 1994-05-31 | Shionogi Seiyaku Kabushiki Kaisha | Pyrrolidylthiocarbapenem derivative |
GB9301276D0 (en) * | 1993-01-22 | 1993-03-17 | Fujisawa Pharmaceutical Co | Bicyclic compounds and their preparation |
WO1995023150A1 (fr) * | 1994-02-25 | 1995-08-31 | Banyu Pharmaceutical Co., Ltd. | Derive de carbapendem |
CZ253698A3 (cs) * | 1996-02-13 | 1999-03-17 | Abbott Laboratories | Deriváty 4-(benzo-1,3-dioxolyl)-pyrrolidin-3-karboxylové kyseliny jako antagonisté endothelinu |
BR9713465A (pt) * | 1996-08-28 | 2000-03-28 | Procter & Gamble | Inibidores metalotprotease de amina cìclica sibstituìda |
BR9712792A (pt) * | 1996-08-28 | 1999-12-14 | Procter & Gamble | Inibidores de metaloprotease bidentada. |
JP3983663B2 (ja) * | 2000-07-19 | 2007-09-26 | エフ.ホフマン−ラ ロシュ アーゲー | メタロプロテアーゼインヒビターとしてのピロリジン誘導体 |
CN1620433A (zh) * | 2000-07-19 | 2005-05-25 | 霍夫曼-拉罗奇有限公司 | 作为内皮肽转化酶抑制剂的吡咯烷衍生物 |
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WO2002008185A1 (en) | 2002-01-31 |
KR100613196B1 (ko) | 2006-08-18 |
US6790860B2 (en) | 2004-09-14 |
PE20020333A1 (es) | 2002-05-10 |
BR0112655A (pt) | 2003-06-24 |
US20040242672A1 (en) | 2004-12-02 |
JP2004504379A (ja) | 2004-02-12 |
US7189756B2 (en) | 2007-03-13 |
JP3983663B2 (ja) | 2007-09-26 |
MXPA03000368A (es) | 2004-09-13 |
EP1303486A1 (en) | 2003-04-23 |
CN1443164A (zh) | 2003-09-17 |
CA2415740A1 (en) | 2002-01-31 |
UY26846A1 (es) | 2002-01-31 |
KR20030024792A (ko) | 2003-03-26 |
PA8522301A1 (es) | 2002-11-18 |
AU7847901A (en) | 2002-02-05 |
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