ZA200404583B - Pyrrolidine and piperidine derivatives as NK1 antagonists. - Google Patents
Pyrrolidine and piperidine derivatives as NK1 antagonists. Download PDFInfo
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- ZA200404583B ZA200404583B ZA200404583A ZA200404583A ZA200404583B ZA 200404583 B ZA200404583 B ZA 200404583B ZA 200404583 A ZA200404583 A ZA 200404583A ZA 200404583 A ZA200404583 A ZA 200404583A ZA 200404583 B ZA200404583 B ZA 200404583B
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- South Africa
- Prior art keywords
- compound
- alkyl
- group
- cycloalkyl
- independently selected
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- 239000005557 antagonist Substances 0.000 title description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title description 12
- 150000003053 piperidines Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 165
- 125000000217 alkyl group Chemical group 0.000 claims description 110
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 37
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- 238000002360 preparation method Methods 0.000 claims description 33
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- -1 -CH Chemical group 0.000 claims description 24
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
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- 238000011924 stereoselective hydrogenation Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 108060008037 tachykinin Proteins 0.000 description 1
- 239000002466 tachykinin receptor agonist Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 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
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-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
- 150000003672 ureas Chemical class 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
Classifications
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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PE20030762A1 (es) * | 2001-12-18 | 2003-09-05 | Schering Corp | Compuestos heterociclicos como antagonistas nk1 |
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EP1622569B1 (en) | 2003-04-24 | 2015-12-02 | Incyte Corporation | Aza spiro alkane derivatives as inhibitors of metallproteases |
AU2004308935A1 (en) * | 2003-12-22 | 2005-07-14 | Schering Corporation | Pharmaceutical compositions |
DE602005025755D1 (de) | 2004-06-04 | 2011-02-17 | Teva Pharma | Irbesartan enthaltende pharmazeutische zusammensetzung |
ES2632413T3 (es) * | 2004-07-01 | 2017-09-13 | Opko Health, Inc. | Derivados de piperidina como antagonistas de NK1 |
AU2012216435B8 (en) * | 2004-07-01 | 2015-02-19 | Opko Health, Inc. | Piperidine derivatives as NK1 antagonists |
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CL2007000945A1 (es) | 2006-04-05 | 2008-01-25 | Schering Corp | Formulacion farmaceutica que comprende una sal cristalina de monohidrato de hidrocloruro de (5s,8s)-8-[[(1r)-1-(3,5-bistrifluorometil)fenil]-etoximetil]-8-fenil-1,7-diaza-espiro[4.5]decan-2-ona; capsula que la contiene; y uso en el tratamiento de la emesis y nausea. |
TW200806666A (en) * | 2006-04-05 | 2008-02-01 | Schering Corp | Salts of 8-[(1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy)-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one and preparation process therefor |
CN101437821B (zh) * | 2006-04-05 | 2014-06-04 | 欧科生医股份有限公司 | 8-[{1-(3,5-双-(三氟甲基)苯基)-乙氧基}-甲基]-8-苯基-1,7-二氮杂-螺[4.5]癸-2-酮的盐酸盐及其制备方法 |
AR066191A1 (es) * | 2007-03-22 | 2009-08-05 | Schering Corp | Proceso e intermediarios para la sintesis de compuestos 8- [ ( 1- (3,5- bis- ( trifluorometil) fenil) - etoxi ) - metil]- 8 fenil - 1,7- diaza - espiro (4, 5) decan -2 ona |
AR065802A1 (es) * | 2007-03-22 | 2009-07-01 | Schering Corp | Formulaciones de comprimidos que contienen sales de 8- [( 1- ( 3,5- bis- (trifluorometil) fenil) -etoxi ) - metil) -8- fenil -1, 7- diaza- spiro [ 4,5] decan -2- ona y comprimidos elaborados a partir de estas |
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KR101834577B1 (ko) | 2009-08-14 | 2018-03-05 | 옵코 헬스, 인크. | 뉴로키닌-1 길항제의 정맥내 제형 |
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WO2013004766A1 (en) | 2011-07-04 | 2013-01-10 | Ferrari Giulio | Nk-1 receptor antagonists for treating corneal neovascularisation |
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CN105017251B (zh) * | 2015-06-30 | 2018-06-29 | 齐鲁制药有限公司 | 一种nk-1受体拮抗剂的制备方法及其中间体 |
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CN105367510B (zh) * | 2015-11-02 | 2017-07-21 | 叶海伟 | 一种(2R,4S)‑3‑Cbz‑2,4‑二苯基‑1,3‑恶唑烷‑5‑酮的制备方法 |
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