TW201040156A - Glucosylceramide synthase inhibitors - Google Patents

Glucosylceramide synthase inhibitors Download PDF

Info

Publication number: TW201040156A
Authority: TW; Taiwan
Prior art keywords: oxy; group; methyl; formula; compound
Prior art date: 2009-02-06

Application number

TW099103670A

Other languages

English (en)

Chinese (zh)

Inventor

Wai Ki Vicky Chan

Hong-Wang Du

Patrick Kearney

Elena S Koltun

Jason August Nachtigall

Kevin Noson

Michael Pack

Steven James Richards

Original Assignee

Exelixis Inc

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.)

2009-02-06

Filing date

2010-02-06

Publication date

2010-11-16

2010-02-06 Application filed by Exelixis Inc filed Critical Exelixis Inc

2010-11-16 Publication of TW201040156A publication Critical patent/TW201040156A/zh

Links

239000003892 ceramide glucosyltransferase inhibitor Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 163
150000003839 salts Chemical class 0.000 claims abstract description 41
239000000203 mixture Substances 0.000 claims abstract description 38
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
201000010099 disease Diseases 0.000 claims abstract description 23
239000003814 drug Substances 0.000 claims abstract description 11
238000004519 manufacturing process Methods 0.000 claims abstract description 4
-1 CrC8 ring-based Chemical group 0.000 claims description 394
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 162
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 102
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 88
125000000217 alkyl group Chemical group 0.000 claims description 87
125000003118 aryl group Chemical group 0.000 claims description 62
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 35
230000015572 biosynthetic process Effects 0.000 claims description 29
125000000623 heterocyclic group Chemical group 0.000 claims description 29
150000001412 amines Chemical class 0.000 claims description 28
238000003786 synthesis reaction Methods 0.000 claims description 28
239000007789 gas Substances 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 24
150000002431 hydrogen Chemical class 0.000 claims description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 20
125000001188 haloalkyl group Chemical group 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
238000011282 treatment Methods 0.000 claims description 14
239000004593 Epoxy Substances 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000004434 sulfur atom Chemical group 0.000 claims description 13
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
125000002619 bicyclic group Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
102220465932 Beta-1,3-glucuronyltransferase LARGE2_R13A_mutation Human genes 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
208000035475 disorder Diseases 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
229940079593 drug Drugs 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
102000004190 Enzymes Human genes 0.000 claims description 6
108090000790 Enzymes Proteins 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
238000005859 coupling reaction Methods 0.000 claims description 6
150000003573 thiols Chemical class 0.000 claims description 6
206010028980 Neoplasm Diseases 0.000 claims description 5
201000011510 cancer Diseases 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000009472 formulation Methods 0.000 claims description 4
229960002442 glucosamine Drugs 0.000 claims description 4
239000000463 material Substances 0.000 claims description 4
229910052707 ruthenium Inorganic materials 0.000 claims description 4
239000004575 stone Substances 0.000 claims description 4
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 3
241000237858 Gastropoda Species 0.000 claims description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 3
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
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239000003085 diluting agent Substances 0.000 claims description 3
150000002305 glucosylceramides Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
208000030159 metabolic disease Diseases 0.000 claims description 3
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230000003197 catalytic effect Effects 0.000 claims description 2
230000001939 inductive effect Effects 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
241000646858 Salix arbusculoides Species 0.000 claims 1
229910052785 arsenic Inorganic materials 0.000 claims 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
208000016097 disease of metabolism Diseases 0.000 claims 1
150000002118 epoxides Chemical group 0.000 claims 1
150000002357 guanidines Chemical class 0.000 claims 1
231100001261 hazardous Toxicity 0.000 claims 1
230000002757 inflammatory effect Effects 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
238000006317 isomerization reaction Methods 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
239000000178 monomer Substances 0.000 claims 1
125000004149 thio group Chemical group *S* 0.000 claims 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
238000009941 weaving Methods 0.000 claims 1
102000044956 Ceramide glucosyltransferases Human genes 0.000 abstract 4
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150000001204 N-oxides Chemical class 0.000 abstract 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 177
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 98
125000001041 indolyl group Chemical group 0.000 description 95
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 75
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 70
238000005481 NMR spectroscopy Methods 0.000 description 60
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 55
239000000243 solution Substances 0.000 description 48
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 41
239000011570 nicotinamide Substances 0.000 description 38
238000005160 1H NMR spectroscopy Methods 0.000 description 36
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 36
235000005152 nicotinamide Nutrition 0.000 description 35
FVAZJGJEENAKRJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)pyridine-3-carboxylic acid Chemical class OC(=O)C1=CC=CN=C1OC1=CC=C(Cl)C=C1 FVAZJGJEENAKRJ-UHFFFAOYSA-N 0.000 description 33
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 31
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 30
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 description 27
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 26
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
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125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 21
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
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MWKFXSUHUHTGQN-UHFFFAOYSA-N n-decyl alcohol Natural products CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 16
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125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000007115 recruitment Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035807 sensation Effects 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
235000015170 shellfish Nutrition 0.000 description 1
230000011664 signaling Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
235000015523 tannic acid Nutrition 0.000 description 1
229940033123 tannic acid Drugs 0.000 description 1
229920002258 tannic acid Polymers 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 description 1
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000000542 thalamic effect Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
RRBYUSWBLVXTQN-VZCHMASFSA-N tricyclene Natural products C([C@@H]12)C3C[C@H]1C2(C)C3(C)C RRBYUSWBLVXTQN-VZCHMASFSA-N 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
150000003648 triterpenes Chemical class 0.000 description 1
UOCLRXFKRLRMKV-UHFFFAOYSA-N trolnitrate phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.[O-][N+](=O)OCCN(CCO[N+]([O-])=O)CCO[N+]([O-])=O UOCLRXFKRLRMKV-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
229940099072 zavesca Drugs 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- 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
- 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
- C07D405/14—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 three or more hetero rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (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)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Emergency Medicine (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

TW099103670A 2009-02-06 2010-02-06 Glucosylceramide synthase inhibitors TW201040156A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US15043409P	2009-02-06	2009-02-06
PCT/US2010/023080 WO2010091104A1 (en)	2009-02-06	2010-02-03	Glucosylceramide synthase inhibitors

Publications (1)

Publication Number	Publication Date
TW201040156A true TW201040156A (en)	2010-11-16

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Application Number	Title	Priority Date	Filing Date
TW099103670A TW201040156A (en)	2009-02-06	2010-02-06	Glucosylceramide synthase inhibitors

Country Status (3)

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AR (1)	AR075367A1 (es)
TW (1)	TW201040156A (es)
WO (1)	WO2010091104A1 (es)

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JO3713B1 (ar)	2013-03-15	2021-01-31	Genzyme Corp	أشكال ملح (s)-كوينوكليدين-3-يل(2-(2-(4-فلوروفينيل)ثيازول-4-يل)بروبان-2-يل)كارباميت
EP3318277A1 (en)	2016-11-04	2018-05-09	Institut du Cerveau et de la Moelle Epiniere-ICM	Inhibitors of glucosylceramide synthase for the treatment of motor neuron diseases
ES3040555T3 (en)	2019-02-04	2025-11-03	Genzyme Corp	Treatment of ciliopathies using inhibitors of glucosylceramide synthase (gcs)
WO2021096239A1 (en) *	2019-11-15	2021-05-20	Yuhan Corporation	Novel derivatives having 1,2,3,4-tetrahydronaphthalene moiety or pharmaceutically acceptable salt thereof and pharmaceutical compositions comprising the same
BR112022009409A2 (pt) *	2019-11-15	2022-08-09	Yuhan Corp	Novos derivados que têm grupamento 2,3-dihidro-1h-indeno ou 2,3-dihidrobenzofurano ou sal farmaceuticamente aceitável dos mesmos e composições farmacêuticas que os compreendem
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US20230212123A1 (en)	2020-04-28	2023-07-06	The Regents Of The University Of Michigan	Pyridine Inhibitors of Glucosylceramide Synthase and Therapeutic Methods Using the Same
WO2022018695A1 (en)	2020-07-24	2022-01-27	Genzyme Corporation	Pharmaceutical compositions comprising venglustat
WO2022060763A2 (en) *	2020-09-17	2022-03-24	Merck Sharp & Dohme Corp.	Modified imidazopyridines as glucosylceramide synthase inhibitors
EP4213832A4 (en) *	2020-09-18	2024-10-16	Merck Sharp & Dohme LLC	Modified benzofuran-carboxamides as glucosylceramide synthase inhibitors
EP4490148A2 (en) *	2022-03-11	2025-01-15	Merck Sharp & Dohme LLC	Non-aromatic cyclic-pyrimidine analogs as glucosylceramide synthase inhibitors
EP4493545A2 (en) *	2022-03-14	2025-01-22	Merck Sharp & Dohme LLC	Fused pyrazole amide analogs as glucosylceramide synthase inhibitors

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US5145684A (en)	1991-01-25	1992-09-08	Sterling Drug Inc.	Surface modified drug nanoparticles
GB0400812D0 (en)	2004-01-14	2004-02-18	Celltech R&D Ltd	Novel compounds
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US8304447B2 (en) *	2007-05-31	2012-11-06	Genzyme Corporation	2-acylaminopropoanol-type glucosylceramide synthase inhibitors

2010
- 2010-02-03 WO PCT/US2010/023080 patent/WO2010091104A1/en not_active Ceased
- 2010-02-05 AR ARP100100326A patent/AR075367A1/es unknown
- 2010-02-06 TW TW099103670A patent/TW201040156A/zh unknown

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WO2010091104A1 (en)	2010-08-12
AR075367A1 (es)	2011-03-30
WO2010091104A8 (en)	2011-04-07

Publication	Publication Date	Title
TW201040156A (en)	2010-11-16	Glucosylceramide synthase inhibitors
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US11186565B2 (en)	2021-11-30	Aromatic compound
DK3031799T3 (en)	2018-05-28	AROMATIC CONNECTION
TW201040149A (en)	2010-11-16	Inhibitors of glucosylceramide synthase
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