KR20040008159A - 스파이로파이라졸 화합물 - Google Patents
스파이로파이라졸 화합물 Download PDFInfo
- Publication number
- KR20040008159A KR20040008159A KR10-2003-7013821A KR20037013821A KR20040008159A KR 20040008159 A KR20040008159 A KR 20040008159A KR 20037013821 A KR20037013821 A KR 20037013821A KR 20040008159 A KR20040008159 A KR 20040008159A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- phenyl
- group
- cycloalkyl
- decan
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- -1 -CH 2 OH Chemical group 0.000 claims description 176
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 15
- 208000002193 Pain Diseases 0.000 claims description 15
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 108010020615 nociceptin receptor Proteins 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 108090000137 Opioid Receptors Proteins 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 102000003840 Opioid Receptors Human genes 0.000 claims description 9
- 230000004044 response Effects 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 230000036407 pain Effects 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 230000000202 analgesic effect Effects 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
- 125000006623 cyclooctylmethyl group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 230000003285 pharmacodynamic effect Effects 0.000 claims 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 34
- 239000001257 hydrogen Substances 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
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- 238000009472 formulation Methods 0.000 description 12
- 150000002431 hydrogen Chemical group 0.000 description 12
- 239000000556 agonist Substances 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- XLQGICHHYYWYIU-UHFFFAOYSA-N veramine Natural products O1C2CC3C4CC=C5CC(O)CCC5(C)C4CC=C3C2(C)C(C)C21CCC(C)CN2 XLQGICHHYYWYIU-UHFFFAOYSA-N 0.000 description 1
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- 229960002110 vincristine sulfate Drugs 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960005212 vindesine sulfate Drugs 0.000 description 1
- BCXOZISMDZTYHW-IFQBWSDRSA-N vinepidine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@H](C2)CC)N2CCC2=C1NC1=CC=CC=C21 BCXOZISMDZTYHW-IFQBWSDRSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
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- 229960002166 vinorelbine tartrate Drugs 0.000 description 1
- GBABOYUKABKIAF-IWWDSPBFSA-N vinorelbinetartrate Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC(C23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IWWDSPBFSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- RKUQLAPSGZJLGP-UHFFFAOYSA-N xibenolol Chemical compound CC1=CC=CC(OCC(O)CNC(C)(C)C)=C1C RKUQLAPSGZJLGP-UHFFFAOYSA-N 0.000 description 1
- 229960002791 zimeldine Drugs 0.000 description 1
- OYPPVKRFBIWMSX-SXGWCWSVSA-N zimeldine Chemical compound C=1C=CN=CC=1C(=C/CN(C)C)\C1=CC=C(Br)C=C1 OYPPVKRFBIWMSX-SXGWCWSVSA-N 0.000 description 1
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- FYQZGCBXYVWXSP-STTFAQHVSA-N zinostatin stimalamer Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1OC1C/2=C/C#C[C@H]3O[C@@]3([C@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(C)C=CC2=C(C)C=C(OC)C=C12 FYQZGCBXYVWXSP-STTFAQHVSA-N 0.000 description 1
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Classifications
-
- 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
- C07D471/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Abstract
본 발명은 다음 화학식 1로 표시되는 화합물을 제공한다.
화학식 1
상기 식에서, Z, W, A, B, C, R1, R2, Q 및 n은 상기에서 정의한 바와 같다.
Description
만성적인 고통은 무력증(disability)을 일으키는 주요 원인이며, 말로 표현할 수 없을 정도의 고통의 원인이다. 바람직한 약물인 오피오이드 진통제를 이용한 이러한 심각하고 만성적인 고통을 성공적으로 치료하는 것이 의사들의 일차적인 목표이다.
최근까지, 중추신경계(central nervous system, CNS)에서 오피오이드 수용체의 세가지의 중요한 종류의 증거가 있었는 바, 이들 각각의 종류는 아류형(subtype) 수용체이다. 이러한 수용체 종은 μ, δ 및 κ로 설계된 것이다. 진정제(opiate)는 이러한 수용체에 높은 친화성을 가지는 반면, 신체에는 내성을 가지지 않기 때문에, 이러한 수용체에 내성을 가지는 리간드를 규명하고 분리시키기 위한 연구들이 이어졌다. 이러한 리간드들은 엔케파린(enkephaline), 엔돌핀(endorphin) 및 다이놀핀(dynorphin)으로 규명된 것들이다.
최근의 실험에서는 잘 알려진 수용체 종(class)에 높은 정도의동족관계(homology)를 가지는 오피오이드 수용체-와 같은 수용체(opioid receptor-like, ORL1)를 암호화하는(encoding) cDNA의 규명을 주도해 왔다. 이렇게 새롭게 발견된 수용체는 구조적인 관점으로만 봤을 때는 오피오이드 수용체로 분류되는 바, 이 수용체가 약리학적 동족관계(homology)를 나타내지 않기 때문이다. μ, δ 및 κ 수용체에 높은 친화성을 가지는 비-선택적 리간드는 초기에는 ORL1 에 대해서 낮은 친화성을 가지는 것으로 나타났다. 내성을 가지는 리간드는 아직 발견된 적이 없다는 사실과 함께, 이러한 특징은 "오펀 수용체(orphan receptor)" 라는 용어를 끌어내었다.
계속해서 ORL1 수용체의 내성을 가지는 리간드의 분리와 구조를 유도하는 연구가 이어졌다. 이 리간드는 17번 단백질 펩타이드로서, 오피오이드 단백질 군(family)의 멤버와 구조적으로 유사하다. ORL1 수용체의 발견으로 신규한 화합물을 이용한 약물의 발견에 이용할 기회를 가지는 바, 이러한 약물을 고통을 다스리는 데 투여되거나 또는 이러한 수용체에 의해 다른 일련의 증후들을 조절할 수 있게 된다.
상기 기술된 것을 포함한, 여기에서 인용된 모든 문헌들은 모은 목적을 위하여 원형 그대로 본 발명의 참고자료로 반영되었다.
본 출원의 청구항은 2001년 4월 18일에 출원된 미국 임시 출원 번호 제 60/284,674호 로부터 우선권을 가지는 것으로, 이들 명세서는 본 발명의 참고자료로 반영되었다.
따라서, 본 발명의 어떤 구현예에서의 목적은 ORL1 수용체에 친화성을 나타내는 신규한 화합물을 제공하는 것이다.
또한, 본 발명의 어떤 구현예에서의 목적은 ORL1 수용체와 1종 또는 그 이상의 μ, δ 및 κ 수용체에 친화성을 나타내는 신규한 화합물을 제공하는 것이다.
본 발명의 어떤 구현예에서의 목적은 ORL1 수용체에 친화성을 가지는 화합물을 만성적인 또는 급성의 고통으로 고생하는 환자에게 투여함으로써 이를 치료하기 위한 새로운 화합물을 제공하는 것이다.
본 발명의 어떤 구현예에서의 목적은 몰핀(morphine)과 같은 현재 상업적으로 구입가능한 화합물보다 μ,δ 및 κ 수용체에서 보다 높은 작동약 활성(agonist activity)을 가지는 새로운 화합물을 제공하는 것이다.
본 발명의 어떤 구현예에서의 목적은 현재 상업적으로 구입가능한 화합물보다 μ,δ 및 κ 수용체에서 보다 높은 작동약 활성을 가지는 새로운 화합물을 투여함으로써 만성적인 또는 급성의 고통을 치료하는 방법을 제공하는 것이다.
본 발명의 어떤 구현예에서의 목적은 현재 상업적으로 구입가능한 화합물보다 부작용이 적고, μ,δ 및 κ 수용체에서 작동약 활성도를 가지는 비-오피오이드계 화합물을 투여함으로써 만성적인 또는 급성의 고통을 치료하는 방법을 제공하는 것이다.
본 발명의 어떤 구현예에서의 목적은 진통제, 항-염증제(anti-inflammatory), 이뇨제(diuretic), 마취제(anesthetic), 및 신경보호제(neuroprotective agents), 항-고혈압(anti-hypertensive), 항-불안완화제(anti-anxioltics); 식욕 억제제(agent for appetite control); 청력 조절제(hearing regulators); 항-기침성(anti-tussive), 항-천식성(anti-asthmatics), 이동 활성의 조절(modulators of locomotor activity), 학습 및 기억력의 조절(modulators of learning and memory), 신경전달물질 및 호르몬 방출의 조절, 신장 기능 조절, 항-진정제(anti-depressant), 알츠하이머병 또는 다른 치매로 인한 기억력 손실을 치료하는 약물, 항-간질병(anti-epileptics), 항-경련제(anti-convulsant), 알콜 및 약물 중독으로부터 금단 증상을 치료하기 위한 약물, 수분 밸런스 조절 약물, 소듐 배출 치료용 약물 및 동맥의 혈압 이상을 조절하기 위한 약물과 같은 곳에 유용한 화합물과 및 상기 이러한 화합물을 투여하기 위한 방법을 제공하는 데 있다.
본 발명의 화합물은 1종 또는 그 이상의 오피오이드 수용체(ORL-1, μ,δ 및 κ)를 이용하여 중추로부터 및/또는 말초로부터 약물동력학적 반응을 조절하는 데 유용하다. 이러한 응답은 1종 또는 그 이상의 수용체를 자극하거나(작동약) 또는 억제하는데(길항근) 기여할 수 있다. 어떤 화합물은 한 수용체(예를 들면, μ 작동약)를 자극시킬 수 있으며, 다른 수용체(예를 들면, ORL-1 길항근)를 억제시킨다.
본 발명의 어떤 구현예에서는 다음 화학식 1로 표시되는 화합물을 포함한다:
[화학식 1]
여기서, W는 수소, 탄소수 1 내지 10의 알킬, 탄소수 3 내지 12의 사이클로알킬, 탄소수 3 내지 12의 사이클로알킬C1-4알킬-, 탄소수 1 내지 10의 알콕시, 탄소수 3 내지 12의 사이클로알콕시-, 1 내지 3의 할로겐으로 치환된 탄소수 1 내지 10의 알킬, 1 내지 3의 할로겐으로 치환된 탄소수 3 내지 12의 사이클로알킬, 1 내지 3의 할로겐으로 치환된 탄소수 3 내지 12의 사이클로알킬C1-4알킬-, 1 내지 3의 할로겐으로 치환된 탄소수 1 내지 10의 알콕시, 1 내지 3의 할로겐으로 치환된 탄소수 3 내지 12의 사이클로알콕시-, -COOV1, -C1-4COOV1, -CH2OH, -SO2N(V1)2, 하이드록시C1-10알킬-, 하이드록시C3-10사이클로알킬-, 시아노C1-10알킬-, 시아노C3-10사이클로알킬-, -CON(V1)2, NH2SO2C1-4알킬-, NH2SOC1-4알킬-, 설포닐아미노C1-10알킬-, 다이아미노알킬-, -설포닐C1-4알킬, 6-원 헤테로사이클릭 환, 6-원 헤테로방향족 환, 6-원의 헤테로사이클릭C1-4알킬-, 6-원 헤테로방향족C1-4알킬-, 6-원 방향족 환, 6-원 방향족 C1-4알킬-, 옥소 또는 티오로 임의 치환된 5-원 헤테로사이클릭 환, 5-원 헤테로방향족 환, 옥소 또는 티오로 임의 치환된 5-원 헤테로사이클릭 C1-4알킬-, 5-원 헤테로방향족 C1-4알킬-, -C1-5(=O)W1, -C1-5(=NH)W1, -C1-5NHC(=O)W1, -C1-5NHS(=O)2W1, -C1-5NHS(=O)W1이며, 여기서 W1은 수소, 탄소수 1 내지 10의 알킬, 탄소수 3 내지 12의 사이클로알킬, 탄소수 1 내지 10의 알콕시, 탄소수 3 내지 12의 사이클로알콕시, -CH2OH, 아미노, 탄소수 1 내지 4의 알킬아미노-, 다이C1-4알킬아미노-, 또는 1 내지 3의 저급 알킬기로 임의 치환된 5-원 헤테로방향족 환이며;
여기서 각각의 V1은 수소, 탄소수 1 내지 6의 알킬, 탄소수 3 내지 6의 사이클로알킬, 벤질 및 페닐로부터 독립적으로 선택된 것이며;
Q는 탄소수 1 내지 8의 알킬, 5 내지 8원의 사이클로알킬, 5 내지 8-원의 헤테로사이클릭 또는 6-원의 방향족 또는 헤테로방향족 그룹이며;
n은 0 내지 3의 정수이며;
A, B 및 C는 서로 독립적인 것으로, 수소, 탄소수 1 내지 10의 알킬, 탄소수 3 내지 12의 사이클로알킬, 탄소수 1 내지 10의 알콕시, 탄소수 3 내지 12의 사이클로알콕시, -CH2OH, -NHSO2, 하이드록시C1-10알킬-, 아미노카르보닐-, 탄소수 1 내지 4의 알킬아미노카르보닐-, 다이C1-4알킬아미노카르보닐-, 아실아미노-, 아실아미노알킬-, 아미드, 설포닐아미노C1-10알킬-, 또는 A-B는 서로 탄소수 2 내지 6의 브리지를 형성하거나, 또는 B-C는 탄소수 3 내지 7의 브릿지를 형성하거나 또는 A-C는 서로 탄소수 1 내지 5의 브릿지를 형성하며;
Z는 결합 사슬, 탄소수 1 내지 6의 직쇄상 또는 가지상 알킬렌, -NH-, -CH2O-, -CH2NH-, CH2N(CH3)-, -NHCH2-, -CH2CONH-, -NHCH2CO-, -CH2CO-, -COCH2-, -CH2COCH2-, -CH(CH3)-, -CH=, -O- 및 -HC=CH-으로 구성된 그룹으로부터 선택된 것이며, 여기서 탄소 및/또는 질소 원자는 1종 또는 그 이상의 저급 알킬, 하이드록시, 할로 또는 알콕시 그룹으로 치환되거나 또는 치환되지 않은 것이며;
R1은 수소, 탄소수 1 내지 10의 알킬, 탄소수 3 내지 12의 사이클로알킬, 탄소수 2 내지 10의 알케닐, 아미노, 탄소수 1 내지 10의 알킬아미노-, 탄소수 3 내지 12의 사이클로알킬아미노-, -COOV1, -C1-4COOV1, 시아노, 시아노C1-10알킬-, 시아노C3-10사이클로알킬-, NH2SO2-, NH2SO2C1-4알킬-, NH2SOC1-4알킬-, 아미노카르보닐-, 탄소수 1 내지 4의 알킬아미노카르보닐-, 다이C1-4알킬아미노카르보닐-, 벤질, 탄소수 3 내지 12의 사이클로알케닐-, 모노사이클릭, 바이사이클릭 또는 트리사이클릭 아릴 또는 헤테로아릴 환, 헤테로모노사이클릭 환, 헤테로-바이사이클릭 환 시스템 및 다음 화학식 2로 표시되는 스파이로 환 시스템으로 구성된 그룹으로부터 선택된 것이며;
[화학식 2]
여기서 X1및 X2는 서로 독립적인 것으로, NH, O, S 및 CH2로 구성된 그룹으로부터 선택된 것이며, 여기서 상기 R1의 알킬, 사이클로알킬, 알케닐, 탄소수 1 내지 10의 알킬아미노-, 탄소수 3 내지 12의 사이클로알킬아미노-, 또는 벤질은 할로겐, 하이드록시, 탄소수 1 내지 10의 알킬, 탄소수 1 내지 10의 알콕시, 니트로, 트리플루오로메틸-, 시아노, -COOV1, -탄소수 1 내지 4의 COOV1, 시아노C1-10알킬-, -C1-5(=O)W1, -C1-5NHS(=O)2W1, -C1-5NHS(=O)W1, 5-원 헤테로방향족C0-4알킬-, 페닐, 벤질, 벤질옥시로 구성된 그룹으로부터 선택된 1 내지 3이 치환기로 임의 치환된 것이며, 여기서 페닐, 벤질, 및 벤질옥시는 할로겐, 탄소수 1 내지 10의 알킬-, 탄소수 1 내지 10의 알콕시-, 및 시아노기로 구성된 그룹으로부터 선택된 1 내지 3의 치환체로 임의 치환된 것이며; 및 여기서 탄소수 3 내지 12의 사이클로알킬, 탄소수 3 내지 12의 사이클로알케닐, 모노사이클릭, 바이사이클릭 또는 트리사이클릭 아릴, 헤테로아릴 환, 헤테로-모노사이클릭 환, 헤테로-바이사이클릭 환 시스템 또는 상기 화학식 2의 스파이로 환 시스템은 할로겐, 탄소수 1 내지 10의 알킬, 탄소수 1 내지 10의 알콕시, 니트로, 트리플루오로메틸-, 페닐, 벤질, 페닐옥시 및 벤질옥시로 구성된 그룹으로부터 선택된 1 내지 3의 치환체로 임의 치환된 것이며, 여기서 상기 페닐, 벤질, 페닐옥시 또는 벤질옥시는 할로겐, 탄소수 1 내지 10의 알킬, 탄소수 1 내지 10의 알콕시, 및 시아노기로 구성된 그룹으로부터 선택된 1 내지 3의 치환기로 임의 치환된 것이며;
R2는 수소, 탄소수 1 내지 10의 알킬, 탄소수 3 내지 12의 사이클로알킬- 및 할로겐으로 구성된 그룹으로부터 선택된 것이며, 여기서 알킬 또는 사이클로알킬은 옥소, 아미노, 알킬아미노 또는 다이알킬아미노 그룹으로 임의 치환된 것이며;
및 약학적으로 용인된 이들의 염 및 이들의 용매화합물(solvate)이다.
본 발명의 한 구현예에서는 다음 화학식 3으로 표시되는 화합물을 포함한다:
[화학식 3]
여기서, n은 0 내지 3의 정수이며;
Z는 결합사슬, -CH2-, -NH-, -CH2O-, -CH2CH2-, -CH2NH-, -CH2N(CH3)-, -NHCH2-, -CH2CONH-, -NHCH2CO-, -CH2CO-, -COCH2-, -CH2COCH2-, -CH(CH3)-, -CH=, 및 -HC=CH- 으로 구성된 그룹으로부터 선택된 것이며, 여기서 탄소 및/또는 질소 원자는 저급 알킬, 할로겐, 하이드록시 또는 알콕시 그룹으로 치환되거나 또는 치환되지 않은 것이며;
R1은 수소, 탄소수 1 내지 10의 알킬, 탄소수 3 내지 12의 사이클로알킬, 탄소수 2 내지 10의 알케닐, 아미노, 탄소수 1 내지 10의 알킬아미노, 탄소수 3 내지 12의 사이클로알킬아미노, 벤질, 탄소수 3 내지 12의 사이클로알케닐, 모노사이클릭, 바이사이클릭 또는 트리사이클릭 아릴 또는 헤테로아릴 환, 헤테로-모노사이클릭 환, 헤테로-바이사이클릭 환 시스템 및 다음 화학식 2로 표시되는 스파이로 환 시스템으로 구성된 그룹으로부터 선택된 것이며;
화학식 2
여기서 X1및 X2는 서로 독립적인 것으로, NH, O, S 및 CH2로 구성된 그룹으로부터 선택된 것이며;
여기서 상기 모노사이클릭 아릴은 페닐이 바람직하며; 여기서 상기 바이사이클릭 아릴은 나프틸기가 바람직하며; 여기서 상기 알킬, 사이클로알킬, 알케닐, 탄소수 1 내지 10의 알킬아미노, 탄소수 3 내지 12의 사이클로알킬아미노, 또는 벤질은 할로겐, 탄소수 1 내지 10의 알킬, 탄소수 1 내지 10의 알콕시, 니트로, 트리플루오로메틸, 시아노, 페닐, 벤질, 벤질옥시로 구성된 그룹으로부터 선택된 1 내지 3의 치환기로 임의 치환된 것이며, 여기서 페닐, 벤질 및 벤질옥시는 할로겐, 탄소수 1 내지 10의 알킬, 탄소수 1 내지 10의 알콕시 및 시아노기로 구성된 그룹으로부터 선택된 1 내지 3의 치환기로 임의 치환된 것이며;
여기서 상기 탄소수 3 내지 12의 사이클로알킬, 탄소수 3 내지 12의 사이클로알케닐, 모노사이클릭, 바이사이클릭 또는 트리사이클릭 아릴, 헤테로아릴 환, 헤테로-모노사이클릭 환, 헤테로-바이사이클릭 환 시스템 및 상기 화학식 2의 스파이로 환 시스템은 할로겐, 탄소수 1 내지 10의 알킬, 탄소수 1 내지 10의 알콕시, 니트로, 트리플루오로메틸, 페닐, 벤질, 페닐옥시 및 벤질옥시로 구성된 그룹으로부터 선택된 1 내지 3의 치환기로 임의 치환된 것이며, 여기서 페닐, 벤질 및 페닐옥시 및 벤질옥시는 할로겐, 탄소수 1 내지 10의 알킬, 탄소수 1 내지 10의 알콕시 및 시아노기로 구성된 그룹으로부터 선택된 1 내지 3의 치환기로 임의 치환된 것이며;
R2는 수소, 탄소수 1 내지 10의 알킬, 탄소수 3 내지 12의 사이클로알킬 및 할로겐으로 구성된 그룹으로부터 선택된 것으로, 여기서 알킬은 옥소 그룹으로 임의 치환된 것이며; 및 약학적으로 용인된 이들의 염 및 용매화합물이다.
어떤 바람직한 구현예의 화학식 1 또는 화학식 3에서, Q는 페닐 또는 질소 원자 1 내지 3을 포함하는 6원의 헤테로방향족 그룹이다.
어떤 바람직한 구현예의 화학식 1 또는 3에서, R1의 알킬은 메틸, 에틸, 프로필, 부틸, 펜틸 또는 헥실이다. 어떤 바람직한 구현예의 화학식 1 또는 3에서, R1의 사이클로알킬은 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 사이클로노닐, 사이클로데실, 또는 노보닐이다. 다른 바람직한 구현예의 화학식 1 또는 3에서, R1의 바이사이클릭 환 시스템은 나프틸이다.
다른 바람직한 구현예의 화학식 1 또는 3에서, R1의 바이사이클릭 환 시스템은 테트라히드로나프틸, 또는 데카히드로나프틸이고, R1의 트리사이클릭 환 시스템은 다이벤조사이클로헵틸이다. 다른 바람직한 구현예에서 R1은 페닐 또는 벤질이다. 다른 바람직한 구현예의 화학식 1 또는 3에서, R1의 바이사이클릭 방향족 환은 10-원(10-membered)의 환, 바람직하기로는 퀴놀린(quinoline) 또는 나프틸(naphthyl)이다. 다른 바람직한 구현예의 화학식 1 또는 3에서, R1의 바이사이클릭 방향족 환은 9-원의 환, 바람직하기로는 인데닐(indenyl)이다. 다른 바람직한 구현예의 화학식 1 또는 3에서, Z는 결합 사슬, 메틸 또는 에틸기이다.
다른 바람직한 구현예의 화학식 1 또는 3에서, Z 그룹은 기본 Z 그룹에 어떤 수소 치환기도 가지지 않는 것과 같이 최대로 치환된 것이다. 예를 들면, 만일 기본적인 Z 그룹은 -CH2- 이라면, 두개의 메틸 그룹으로 치환된 것은 기본적인 Z 그룹 -CH2- 로부터 수소는 제거될 것이다.
어떤 바람직한 구현예의 화학식 1 또는 3에서, n은 0이다.
어떤 바람직한 구현예의 화학식 1 또는 3에서, X1및 X2는 모두 0이다.
어떤 바람직한 구현예의 화학식 1에서, W는 -CH2C(=O)NH2, -C(NH)NH2, 피리딜메틸(pyridylmethyl), 사이클로펜틸(cyclopentyl), 사이클로헥실(cyclohexyl), 푸라닐메틸(furanylmethyl), -C(=O)CH3, -CH2CH2NHC(=O)CH3, -SO2CH3, CH2CH2NHSO2CH3, 푸라닐카르보닐-(furanylcarbonyl-), 메틸피롤일카르보닐(methylpyrrolylcarbonyl-), 다이아졸카르보닐-(diazolecarbonyl-), 아졸메틸(azolemethyl-), 트리플루오로에틸-(trifluoroethyl-), 하이드록시에틸-, 시아노메틸-, 옥소옥사졸메틸-(oxooxazolemethyl-), 또는 다이아졸메틸(diazolemethyl-)이다.
어떤 바람직한 구현예에서, 화학식 1의 ZR1은 사이클로헥실에틸-, 사이클로헥실메틸-, 사이클로펜틸메틸-, 다이메틸사이클로헥실메틸-, 페닐에틸-, 피롤일트리플루오로에틸-, 티에닐트리플루오로에틸-(thienyltrifluoroethyl-), 피리딜에틸-, 사이클로펜틸-, 사이클로헥실-, 메톡시사이클로헥실-, 테트라하이드로피라닐-, 프로필피페리디닐-, 인돌일메틸-(indolylmethyl-), 피라조일펜틸-, 티아졸일에틸-, 페닐트리플루오로에틸-, 하이드록시헥실, 메톡시헥실-, 이소프로폭시부틸-, 헥실, 또는 옥소카닐프로필-(oxocanylpropyl) 이다.
어떤 바람직한 구현예에서, 화학식 1의 1종 이상의 ZR1또는 W는 -CH2COOV1, 테트라졸일메틸-, 시아노메틸-, NH2SO2메틸-, NH2SO메틸-, 아미노카르보닐메틸-, 탄소수 1 내지 4의 알킬아미노카르보닐메틸-, 또는 다이C1-4알킬아미노카르보닐메틸- 이다. 어떤 바람직한 구현예에서, 화학식 1의 ZR1은 프로필기의 3번 탄소에 -COOV1, 테트라졸일C0-4알킬-, 시아노-, 아미노카르보닐-, 탄소수 1 내지 4의 알킬아미노카르보닐-, 또는 다이C1-4알킬아미노카르보닐- 로 임의 치환된 3,3 다이페닐프로필이다.
선택적인 구현예에서 화학식 1 또는 3의 ZR1은이며,
여기서, Y1은 R3-(C1-C12)알킬, R4-아릴, R5-헤테로아릴, R6-(C3-C12)사이클로-알킬, R7-(C3-C7)헤테로사이클로알킬, -CO2(C1-C6)알킬, CN 또는 -C(O)NR8R9이며;
Y2는 수소 또는 Y1이고; Y3는 수소 또는 (C1-C6)알킬이며; 또는 Y1, Y2및 Y3는탄소 원자와 서로 연결된 다음과 같은 구조 중의 하나를 가지며:
여기서 r은 0 내지 3이고; w와 u는 각각 o 내지 3이고; w와 u의 합은 1 내지 3이고; c 와 d는 독립적인 것으로 1 또는 2이고; s는 1 내지 5이고; 환 E는 접합된 R4-페닐 또는 R5-헤테로아릴 환이고;
R10은 수소, (C1-C6)알킬, -OR8, -(C1-C6)알킬-OR8, -NR8R9및 -(C1-C6)알킬-NR8R9로 구성된 그룹으로부터 독립적으로 선택된 1 내지 3의 치환기이고;
R11은 R10, -CF3, -OCF3, NO2및 할로로 구성된 그룹으로부터 독립적으로 선택된 1 내지 3의 치환기이거나, 또는 근접된 환의 탄소 원자상의 R11치환기는 메틸렌다이옥시 또는 에틸렌다이옥시 환의 형태로 된 것이며;
R8과 R9는 서로 독립적인 것으로, 수소, (C1-C6)알킬, (C3-C12)사이클로알킬, 아릴 및 아릴(C1-C6)알킬로 구성된 그룹으로부터 선택된 것이며;
R3는 수소, R4-아릴, R6-(C3-C12)사이클로알킬, R5-헤테로아릴, R7-(C3-C7)헤테로사이클로알킬, -NR8R9, -OR12및 -S(O)0-2R12로 구성된 그룹으로부터 독립적으로 선택된 1 내지 3종의 치환기이고;
R6는 수소, (C1-C6)알킬, R4-아릴, -NR8R9, -OR12및 -SR12로 구성된 그룹으로부터 독립적으로 선택된 1 내지 3종의 치환기이고;
R4는 수소, 할로, (C1-C6)알킬, R13-아릴, (C3-C12)사이클로알킬, -CN, -CF3, -OR8, -(C1-C6)알킬-OR8, -OCF3, -NR8R9, -(C1-C6)알킬-NR8R9, -NHSO2R8, -SO2N(R14)2, -SO2R8, -SOR8, -SR8, -NO2, -CONR8R9, -NR9COR8, -COR8, -COCF3, -OCOR8, -OCO2R8, -COOR8, -(C1-C6)알킬-NHCOOC(CH3)3, -(C1-C6)알킬-NHCOCF3, -(C1-C6)알킬-NHSO2-(C1-C6)알킬, -(C1-C6)알킬-NHCONH-(C1-C6)-알킬 및이며,
상기 식에서 f는 0 내지 6이고; 또는 근접된 환의 탄소 원자 상의 R4치환기는 서로 메틸렌다이옥시 또는 에틸렌다이옥시 환을 형성하는 것이며;
R5는 수소, 할로, (C1-C6)알킬, R13-아릴, (C3-C12)사이클로알킬, -CN, -CF3, -OR8, -(C1-C6)알킬-OR8, -OCF3, -NR8R9, -(C1-C6)알킬-NR8R9, -NHSO2R8, -SO2N(R14)2, -NO2, -CONR8R9, -NR9COR8, -COR8, -OCOR8, -OCO2R8및 -COOR8로 구성된 그룹으로부터 선택된 1 내지 3종의 독립된 치환기이고;
R7은 수소, (C1-C6)알킬, -OR8, (C1-C6)알킬-OR8, -NR8R9또는 -(C1-C6)알킬-NR8R9이며;
R12는 수소, (C1-C6)알킬, R4-아릴, -(C1-C6)알킬-OR8, -(C1-C6)알킬-NR8R9, -(C1-C6)알킬-SR8, 또는 아릴(C1-C6)알킬이며;
R13은 수소, (C1-C6)알킬, -(C1-C6)알콕시 및 할로로 구성된 그룹으로부터 선택된 1 내지 3종의 독립된 치환기이며;
R14는 수소, (C1-C6)알킬 및 R13-C6H4-CH2-로 구성된 그룹으로부터 선택된 1 내지 3종의 독립된 치환기이다.
여기에서 사용된 "알킬"이라는 것은 단일 라디칼 및 탄소수 1 내지 10을 가지는 직쇄상 또는 가지상 지방족 탄화수소 그룹을 의미한다. 이러한 알킬 그룹의 예를 들면, 메틸, 프로필, 이소프로필, 부틸, n-부틸, 이소부틸, sec-부틸, tert-부틸, 및 펜틸을 포함한다. 가지상 알킬은 메틸, 에틸 또는 프로필과 같은 1종 또는 그 이상의 알킬 그룹이 직쇄상의 알킬 사슬의 -CH2- 그룹에서 1 또는 2의 수소로 치환되는 것이다. "저급 알킬기"는 탄소수 1 내지 3의 알킬을 의미한다.
"알콕시"라는 것은 상기 정의된 "알킬"기에 산소 라디칼이 연결된 것을 의미한다.
"사이클로알킬"은 단일 라디칼 및 탄소수 3 내지 12를 가지는 비-방향족 모노- 또는 다중사이클릭 탄화수소 환 시스템을 의미한다. 이러한 모노사이클릭 사이클로알킬 환의 예를 들면, 사이클로프로필, 사이클로펜틸 및 사이클로헥실을 포함한다. 또한, 다중사이클릭 사이클로알킬의 예를 들면, 아다만틸 및 노보닐을 포함한다.
"알케닐" 이라는 것은 단일 라디칼 및 탄소수 2 내지 10을 가지는 탄소-탄소간 이중 결합을 포함하는 직쇄상 또는 가지상 지방족 탄화수소 그룹을 의미한다.
"가지상"알케닐은 -CH2-, 또는 -CH= 직쇄상 알케닐 사슬에서 메틸, 에틸 또는 프로필과 같은 1종 또는 그 이상의 알킬 그룹이 1 또는 2개의 수소로 치환된 것을 의미한다. 이러한 알케닐 그룹의 예를 들면, 에테닐, 1- 및 2-프로페닐, 1-, 2- 및 3-부테닐, 3-메틸부트-2-에닐(3-methylbut-2-enyl), 2-프로페닐, 헵테닐, 옥테닐 및 데케닐을 포함한다.
"사이클로알케닐"은 단일 라디칼 및 탄소수 3 내지 12를 가지는 탄소-탄소 이중 결합을 포함하는 비-방향족 모노사이클릭 또는 다중사이클릭 탄화수소 환 시스템을 의미한다. 이러한 모노사이클릭 사이클로알케닐 환의 예를 들면, 사이클로 프로페닐, 사이클로펜테닐, 사이클로헥세닐, 또는 사이클로헵테닐을 포함한다. 또한 다중사이클릭 사이클로알케닐 환의 예를 들면, 노보네닐이 있다.
"아릴"은 펜던트 방법 또는 접합된 형태로 서로 결합된 1, 2, 또는 3개의 환 및 단일 라디칼을 포함하는 카르보사이클릭 방향족 환 시스템을 의미한다. 이러한 아릴 그룹의 예를 들면, 페닐, 나프틸 및 아세나프틸(acenaphthyl)기를 포함한다.
"헤테로사이클릭"은 1종 또는 그 이상의 헤테로원자(탄소 이외의 원자) 및단일 라디칼을 환 내에 포함하고 있는 사이클릭 화합물을 의미한다. 여기서 환은 포화된 것이거나, 부분적으로 포화되거나 또는 포화되지 않은 것이며, 헤테로 원자는 질소, 황 및 산소로 구성된 그룹으로부터 선택된 것이다. 이러한 포화 헤테로사이클릭 라디칼의 예를 들면, 피롤리디닐, 이미다졸리디닐, 피페리디노, 피페라지닐과 같은 질소 원자 1 내지 4를 포함하는 포화 3 내지 6-원의 헤테로-모노사이클릭 그룹이 있으며; 몰포리닐과 같은 산소 원자 1 내지 2와 질소 원자 1 내지 3을 포함하는 포화 3- 내지 6-원 헤테로-모노사이클릭 그룹이 있으며; 티아졸리디닐과 같은 황 원자 1 내지 2 및 질소원자 1 내지 3을 포함하는 포화 3- 내지 6-원 헤테로-모노사이클릭 그룹이 있다. 부분적으로 포화된 헤테로사이클릭 라디칼로는 다이하이드로티오펜, 다이하이드로피란, 및 다이하이드로푸란을 포함한다. 다른 헤테로사이클릭 그룹은 옥소카닐(oxocanyl) 및 티오카닐(thiocanyl)과 같은 헤테로 원자로 치환된 7 내지 10의 탄소 환일 수 있다. 헤테로 원자가 황일 경우에, 황은 티오카닐 다이옥사이드와 같은 황 이산화물일 수 있다.
"헤테로아릴"은 불포화된 헤테로사이클릭 라디칼로서, 여기서 "헤테로사이클릭"은 상기에서 설명한 바와 같다. 이러한 헤테로아릴 그룹의 예를 들면, 피롤일(pyrrolyl), 피리딜(pyridyl), 피리미딜(pyrimidyl) 및 피라지닐(pyrazinyl)과 같은 질소원자 1 내지 4를 포함하는 불포화된 3 내지 6 원의 헤테로-모노사이클릭 그룹으며; 인돌일(indolyl), 퀴놀일(quinolyl) 및 이소퀴놀일(isoquinolyl)과 같은 질소 원자 1 내지 5를 포함하는 불포화 농축 헤테로사이클릭 그룹이 있으며; 푸릴(furyl)과 같은 산소 원자를 포함하는 불포화 3 내지 6 원의 헤테로-모노사이클릭 그룹이 있으며; 티에닐(thienyl)과 같은 황 원자를 포함하는 불포화 3 내지 6원의 헤테로-모노사이클릭 그룹이 있으며; 옥사졸일(oxazolyl)과 같은 산소 원자 1 내지 2와 질소 원자 1 내지 3을 포함하는 불포화된 3 내지 6 원의 헤테로-모노사이클릭 그룹이 있으며; 벤즈옥사졸일(benzoxazolyl)과 같은 산소원자 1 내지 2와 질소 원자 1 내지 3을 포함하는 불포화 농축 헤테로사이클릭 그룹이 있으며; 티아졸일(thiazolyl)과 같은 황 원자 1 내지 2와 질소 원자 1 내지 3을 포함하는 불포화 3 내지 6 원의 헤테로-모노사이클릭 그룹이 있으며; 및 벤즈오타이졸일(benzothiazolyl)과 같은 황 원자 1 내지 2와 질소 원자 1 내지 3을 포함하는 불포화 농축 헤테로사이클릭 그룹이 있다.
"헤테로아릴"은 또한 불포화 헤테로사이클릭 라디칼을 포함하는 바, 여기서 "헤테로사이클릭"은 상기에서 기술한 바와 같으며, 여기서 헤테로사이클릭 그룹은 아릴 그룹과 접합한 것이며, 아릴 그룹은 상기에서 기술한 바와 같다. 이러한 접합된 라디칼의 예를 들면, 벤조푸란(benzofuran), 벤즈다이옥솔(benzdioxole), 및 벤조티오펜(benzothiophene)을 포함한다.
여기에서 사용된 것과 같이 "헤테로사이클릭C1-4알킬", "헤테로방향족C1-4알킬" 등은 C1-4알킬 라디칼에 결합된 환 구조를 의미한다.
여기에서 기술된 모든 사이클릭 환의 구조는 결합가능한 어떤 형태로도 결합될 수 있다는 것을 이 분야의 능숙한 기술자들은 알 수 있을 것이다.
여기에서 기술된 것처럼, "환자"는 인간 또는 동물 종 또는 가축과 같은 동물을 포함한다.
또한, 여기에서 기술된 것처럼, "할로겐"은 플로라이드, 브로마이드, 클로라이드, 요오다이드 또는 알라바마이드(alabamide)를 포함한다.
여기에 기술된 본 발명은 여기에서 기술된 화합물의 모든 약학적으로 용인된 이들의 염을 포함하는 것을 의미한다. 약학적으로 용인된 염은, 소듐 염, 포타슘염, 세슘 염 등과 같은 금속 염; 칼슘 염, 마그네슘 염 등과 같은 알칼리 토금속; 트리에틸아민 염, 피리딘 염, 피콜린 염, 에탄올아민 염, 트리에탄올아민 염, 다이사이클로헥실아민 염, N,N'-다이벤질에틸렌다이아민 염 등과 같은 유기 아민 염; 하이드로클로라이드, 하이드로브로마이드, 설페이트, 포스페이트 등과 같은 무기산 염; 포메이트(formate), 아세테이트, 트리플루오로아세테이트, 말레에이트, 푸마레이트, 탈트레이트 등과 같은 유기 산 염; 메탄설포네이트, 벤젠설포네이트, p-톨루엔설포네이트 등과 같은 설포네이트; 알지네이트, 아스파라기네이트, 글루타메이트 등과 같은 아미노산 염을 포함하는 바, 이에 한정되는 것은 아니다.
여기에서 기술된 발명은 또한, 여기에서 기술된 화합물의 모든 프로드러그를 포함한다. 프로드러그는 생체 내에서 활성 모체 약물을 방출하는 공유적으로 결합된 어떤 담체(carrier)도 고려될 수 있다.
여기에서 기술된 발명은 또한, 여기에서 기술된 화합물의 생체 내 신진대사에 의한 생성물까지도 포함되는 것을 의미한다. 이러한 생성물은 화합물을 투여하여 산화, 환원, 가수분해, 아미드화 반응, 에스테르 반응 등과 같은 반응의 결과로 생성된 것으로, 일차적으로 효소에 의한 반응 때문이다. 따라서, 본 발명은 본 발명의 화합물이 그 내부의 신진대사에 의한 생성물을 생성할 수 있는 충분한 시간 주기 동안 포유동물과 접촉하는 것을 포함하는 과정에 의해 생성된 것이다. 이러한 생성물은 일반적으로, 본 발명의 방사성 동위원소를 써서 식별한 화합물을 제조하고, 그것을 쥐, 생쥐, 기니, 돼지, 원숭이같은 동물 또는 사람에게 식별가능한 양의 도스로 비경구로 투여한 다음, 신진대사가 일어나도록 충분한 시간 동안 방치시킨 다음, 소변, 혈액 또는 다른 생물학적인 샘플로부터 그 전환된 생성물을 분리시킴으로써 규명될 수 있다.
여기에서 기술된 본 발명은, 또한 다른 원자량 또는 원자 번호를 가지는 원자에 의해 치환된 1종 또는 그 이상의 원자를 가지는 방사성 동위원소로 식별할 수 있는 화합물을 기술한 것까지도 포함되는 것을 의미한다. 기술된 화합물 내로 병합될 수 있는 이러한 동위원소의 예를 들면, 수소, 탄소, 질소, 산소, 인, 플루오르 및 염소의 동위원소를 포함하는 바, 예를 들면, 각각2H,3H,13C,14C,15N,18O,17O,31P,32P,35S,18F, 및36Cl이다. 여기에서 기술된 화합물의 몇몇은 1종 또는 그 이상의 비대칭 중심을 포함하는 바, 따라서 거울상 이성질체, 부분입체이성질체 및 다른 입체이성질체 형태를 생성시킬 수 있다. 본 발명은 또한, 이들의 라세미 및 리졸브드(resolved) 형태뿐만 아니라 이들의 혼합과 같은 모든 가능한 형태까지 포함한다는 것을 의미한다. 여기에서 기술된 화합물이 올레핀 이중 결합 또는 다른 기하학적 비대칭 중심을 가질 때에는, 특별히 달리 언급하지 않는 한, 이는 E 및 Z 기하 이성질체를 포함하는 것을 의미한다. 모든 토토머들은 본 발명에 의한 것까지포함한다. 여기에서 사용된 것과 같은, "입체이성질체"는 각각의 분자들의 모든 이성질체에 대한 일반적인 용어로서, 이들의 원자들이 공간에서 배열된 것과는 다른 것이다. 이는 하나 이상의 키랄 중심을 가지는 화합물의 거울상이성질체 및 이성질체를 포함하는 바, 이는 서로 거울상은 아니다.(부분입체이성질체)
"키랄 중심"은 네 개의 다른 그룹이 치환된 탄소 원자를 의미한다.
"거울상 이성질체" 또는 "거울상이성질체의"는 그의 거울상이 nonsuperimposeable 이므로, 광학적으로 활성을 가지며, 여기서 거울상 이성질체는 편광된 빛의 면에서 한 방향으로 회전하며, 이의 거울상은 편광된 빛의 면의 반대방향으로 회전한다.
"라세미(racemic)"는 거울상이성질체의 동일한 부분의 혼합물을 의미하는 것으로, 광학적으로는 비활성이다.
"해상도(resolution)"는 분자의 2개의 거울상이성질체 형태 중의 하나의 분리(separation) 또는 선광(concentration) 또는 소모(depletion)를 의미한다.
ORL-1 수용체와 관련된 "조절한다(modulate)"는 것은 환자에 있어서 약물동력학적 반응(예를 들면, 무통각)의 i )수용체의 억제 또는 활성, 또는 (ii)수용체 활성의 정상적인 조절에 직접적으로 또는 간접적으로 영향을 미치는 것으로부터 조정(mediation)을 의미한다. 이러한 수용체 활성을 조절하는 화합물은 작용약, 길항근, 작용약/길항근의 혼합물 및 수용체 활성의 조절에 직접적으로 또는 간접적으로 영향을 미치는 화합물을 포함한다.
본 발명에 따른 바람직한 화합물은 다음을 포함한다:
8-(4-프로필사이클로헥실)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(5-메틸헥스-2-일)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-노보닐-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(데카하이드로-2-나프틸)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(사이클로옥틸메틸)-1-페닐-2,3,8-트리아코스파이로[4.5]데칸-4-온;
8-(1,2,3,4-테트라하이드로-2-나프틸)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-[4-(2-프로필)-사이클로헥실]-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(1,3-다이하이드로인덴-2-일)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-[(나프트-2-일-메틸)]-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(p-페닐벤질)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-[4,4-비스(4-플로로페닐)부틸]-1-페닐-2,3,8-트리아조스파이로[4,5]데칸-4-온;
8-(벤질)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(10,11-다이하이드로-5H-다이벤조[a,d]-사이클로펜텐-5-일)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(3,3-비스(페닐)프로필)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(p-벤질옥시벤질)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온;
8-(사이클로옥틸메틸)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온; 및
약학적으로 용인된 이들의 염 및 이들의 용매화합물.
다른 바람직한 화합물로는 8-(아세나프텐-9-일)-1-페닐-2,3,8-트리아조스파이로[4.5]데칸-4-온 및 약학적으로 용인된 이들의 염 및 이들의 용매화합물이다.
본 발명은 또한 ORL1 수용체와 같은 오피오이드 수용체에 의해 조절해야 하는 고통 및 다른 질병 상태를 치료하기 위한 약물의 제조하는 데도 상기 기술된 화합물의 어떤 것을 사용하는 것도 제공한다. 본 발명의 화합물들은 오피오이드 및 ORL1 수용체의 조절을 필요로 하는 어떤 사람에게든지 투여될 수 있다. 이러한 투여는 경구로, 피부를 통해서, 좌약으로, 흡입제 또는 비 경구를 통해서이다.
본 발명은 또한, 상기 기술한 화합물들의 약학적으로 용인된 모든 염들까지도 포함된다. 이 분야의 능숙한 기술자들은 여기에서 청구된 화합물들의 산 첨가염은 잘 알려진 다양한 방법을 통해 상기 화합물과 적절한 산이 반응함으로써 제조될수 있다는 것을 인식할 수 있을 것이다.
다양한 경구용 제형이 사용될 수 있는 바, 정제, 겔캡스(gelcaps), 캡슐, 캐플릿(caplet), 그래뉼, 마름모꼴 정제(lozenge) 및 벌크 파우더와 같은 고체 형태 및 에멀젼, 용액 및 현탁액과 같은 액상의 형태를 포함한다. 본 발명의 화합물은 단독으로 투여하거나 또는 이 분야의 능숙한 기술자들에게 잘 알려진 약학적으로 용인된 다양한 담체 및 부형제와 함께 조합하여 투여할 수 있는 바, 이러한 담체 및 부형제의 예를 들면, 희석제, 현탁제, 용해제, 바인더, 붕해제, 방부제, 착색제, 윤활제 등이 있지만, 이에 한정되는 것은 아니다. 본 발명의 화합물을 경구용정제 내로 병합시킬 때에는, 이러한 정제는 압축되거나, 습제 정제(tablet triturate), 장-코팅된, 당-코팅된, 필름-코팅된, 다수로 압축된 또는 다수의 층을 이룬 구조의 형태 등이 가능하다. 액상 경구용 제형은 수성 및 비수성 용액, 에멀젼, 현탁액 및 적합한 용매, 방부제, 에멀전화제, 현탁제, 희석제, 감미료(sweetener), 착색제 및 방향제를 포함하는 비-비등성 그래뉼(non-effervescent granule)로부터 재조합된 용액 및/또는 현탁액을 포함한다.
본 발명의 화합물이 비경구로 주입될 때에는, 등장성 살균 용액(isotonic sterile solution)의 형태와 같은 것일 수도 있다. 선택적으로, 본 발명의 화합물을 흡입함으로써 주입시킬 때에는, 건조 에어로졸 내로 처방하거나 또는 수성 또는 부분적인 수성 용액 내로 처방할 수 있다.
추가로, 본 발명의 화합물을 경구용 제형으로 병합될 때에는, 이러한 제형은 위장관에서 화합물이 즉방성을 제공하거나 또는 선택적으로 위장관을 통해서 조절방출성 및/또는 서방성을 제공할 수 있도록 고려할 수 있다. 다양한 조절방출성 및/또는 서방성 제제는 이 분야의 능숙한 기술자들에게 잘 알려진 것이며, 이를 본 발명의 제제와 관련시켜 사용할 수 있을 것이다. 또한, 조절방출성 및/또는 서방성은 경구용 제형을 코팅하거나 또는 본 발명의 화합물을 조절방출성 및/또는 서방성 매트리스 내로 병합시킴으로써 제공될 수도 있을 것이다.
경구용 제형에 제제화되는 데 사용될 수 있는 약학적으로 용인된 담체 및 부형제의 구체적인 예들은약학적 부형제 편람, 미국 약학회(1986)에 기술되어 있다. 경구용 고형 제형을 제조하는 기술과 조성은 Marcel Dekker 사에서 편찬된약학적제형:정제(Lieberman, Lachman 및 Schwartz, editors)의 제 2판에 기술되어 있다. 정제(압축된 및 주형된), 캡슐(하드 및 소프트 젤라틴) 및 환약(pill)을 제조하는 기술과 조성은레밍턴스 약제 과학(Arthur Osol, editor), 15553B1593(1980)에 기술되어 있다. 액상 경구용 제형을 제조하는 기술 및 조성은 Marcel Dekker사에서 편찬된약학적 제형 : 분산 시스템(Lieberman, Rieger and Banker, editors)에 기술되어 있다.
본 발명의 화합물을 주입(연속된 주입 또는 큰 알약으로 주입)을 통해서 비경구로 투여될 경우에는, 비경구 투여용 제제는 유성 또는 수성 부형제 내의 현탁액, 용액, 에멀젼의 형태일 수 있으며, 이러한 제제는 추가로 안정화제, 현탁액제, 분산제 등과 같은 약학적으로 필요한 첨가제를 더 포함할 수 있다. 본 발명의 화합물은 또한 주입가능한 제제로서 재조합된 파우더 형태인 것도 가능하다.
어떤 구현예에서, 본 발명의 화합물은 1종 이상의 다른 치료 약물과 혼합하여 사용될 수 있다. 이러한 치료 약물은 μ-오피오이드 작용약; 비-오피오이드 진통제; 비-스테로이드 항염증성 약물; Cox-Ⅱ 억제제; 제토제(antiemetics); β-아드레날린성 차단제(β-adrenergic blocker); 항경련약(anticonvulsant); 항울약(antidepressant); Ca2+- 채널 차단제; 항암제 및 이들의 혼합물을 포함하지만, 이에 한정되는 것은 아니다.
어떤 구현예에서, 본 발명의 화합물은 μ-오피오이드 작용약과 조합으로 약학적 제형 내로 제제화될 수 있다. 본 발명의 제제 내에 포함될 수 있는 μ-오피오이드 작용약은, 알페타닐(alfentanil), 알릴프로딘(allylprodine),알파프로딘(alphaprodine), 아닐러리딘(anileridine), 벤질몰핀(benzylmorphine), 벤지트라미드(benzitramide), 부푸레놀핀(buprenorphine), 부토판올(butorphanol), 클로니타젠(clonitazene), 코데인(codeine), 데소몰핀(desomorphine), 덱스트로몰아미드(dextromoramide), 데조신(dezocine), 디암프로마이드(diampromide), 디아몰폰(diamorphone), 다이하이드로코데인(dihydrocodeine), 다이하이드로몰핀(dihydromorphine), 다이메녹사돌(dimenoxadol), 다이메펩타놀(dimepheptanol), 다이메틸티암부텐(dimethylthiambutene), 다이옥사페틸 부티레이트(dioxaphetyl butyrate), 다이피파논(dipipanone), 엡타조신(eptazocine), 에토헵타진(ethoheptazine), 에틸메틸티암부텐(ethylmethylthiambutene), 에틸몰핀(ethylmorphine), 에토니타젠펜타닐(etonitazene fentanyl), 헤로인(heroin), 하이드로코돈(hydrocodone), 하이드로몰폰(hydromorphone), 하이드록시페티딘(hydroxypethidine), 아이소메타돈(isomethadone), 케토베미돈(ketobemidone), 레버판올(levorphanol), 레보펜아실몰판(levophenacylmorphan), 로펜타닐(lofentanil), 메페리딘(meperidine), 멥타지놀(meptazinol), 메타조신(metazocine), 메타돈(methadone), 메토폰(metopon), 몰핀(morphine), 미로핀(myrophine), 날부핀(nalbuphine), 나르세인(narceine), 니코몰핀(nicomorphine), 놀레버판올(norlevorphanol), 놀메타돈(normethadone), 날올핀(nalorphine), 놀몰핀(normorphine), 오피움(opium), 옥시코돈(oxycodone), 옥시몰폰(oxymorphone), 파파베레텀(papaveretum), 펜타조신(pentazocine), 페나독손(phenadoxone), 페노몰판(phenomorphan), 페나조신(phenazocine), 페노페리딘(phenoperidine), 피미노딘(piminodine), 피리트라미드(piritramide), 프로헵타진(proheptazine), 프로메돌9promedol), 프로페리딘(properidine), 프로피람(propiram), 프로폭시펜(propoxyphene), 수펜타닐(sufentanil), 티리딘(tilidine), 트라마돌(tramadol), 약학적으로 용인된 이들의 염 및 이들의 혼합물을 포함하지만, 이에 한정되는 것은 아니다.
본 발명의 바람직한 구현예에서, μ-오피오이드 작동약은 코데인(codeine), 하이드로몰폰, 하이드로코돈, 옥시코돈, 다이하이드로코데인, 다이하이드로몰핀, 몰핀, 트라마돌, 옥시몰폰, 약학적으로 용인된 이들의 염 및 이들의 혼합물로부터 선택된 것이다.
본 발명의 다른 구현예에서, 약물은 고통 및/또는 염증을 치료하기 위하여 Cox-Ⅱ 억제제와 5-립옥시제나스(5-lipoxygenase)의 혼합물을 포함한다. 적합한 Cox-Ⅱ 억제제와 5-립옥시제나스 억제제 뿐만 아니라 이들의 조합은 미국 특허 제 6,136,839호에 기술되어 있으며, 이 자료는 원형 그대로 본 발명의 참고자료로 반영되었다. Cox-Ⅱ 억제제는 로페코십(rofecoxib)(Vioxx), 셀레코십(celecoxib)(Celebrex), DUP-697, 플로술라이드(flosulide), 멜록시캄(meloxicam), 6-MNA, L-745337, 나부메톤(nabumetone), 니메술리드(nimesulide), NS-398, SC-5766, T-614, L-768277, GR-253035, JTE-522, RS-57067-000, SC-58125, SC-078, PD-138387, NS-398, 플로술라이드(flosulide), D-1367, SC-5766, PD-164387, 에토리코십(etoricoxib), 발데코십(valdecoxib) 및파레코십(parecoxib) 또는 약학적으로 용인된 이들의 염, 이들의 거울상 이성질체 또는 토토머(tautomers)를 포함하지만, 이에 한정되는 것은 아니다.
본 발명의 화합물은 비-스테로이드계 항-염증성 약물과 같은 비-오피오이드 진통제와 제형 내에서 조합될 수 있는 바, 이러한 비-스테로이드계 항-염증성 약물은 아스피린, 이부프로펜, 다이클로페낙, 나프록센, 베녹사프로펜, 플루비프로펜, 페노프로펜, 플루부펜, 케토프로펜, 인도프로펜, 피로프로펜, 카프로펜, 옥사프로진, 프라모프로펜, 무로프로펜, 트리옥사프로펜, 수프로펜, 아미노프로펜, 티아프로페닉산, 플루프로펜, 부클로식산(bucloxic acid), 인도메타신, 수린닥, 톨메틴, 조메피락, 티오피낙, 지도메타신, 아세메타신, 펜티아작, 클리다낙, 옥스피낙, 메펜아믹 산, 메클로펜아믹산, 플루펜아믹산, 니플루믹산, 톨펜아믹 산, 디플루리살, 플루페니살, 피록시캄, 수독시캄 또는 아이소시캄, 약학적으로 용인된 이들의 염, 및 이들의 혼합물을 포함한다.
본 발명의 제형 내로 포함될 수 있는 다른 적절한 비-오피오이드 진통제는 다음을 포함하지만, 이에 한정되는 것은 아니다. 진통제, 해열제, 비스테로이드계 항염증성 약물의 화학 종: 아스피린, 소듐 살리실레이트, 콜린 마그네슘 트리살리실레이트, 살살레이트, 다이플루니살, 살리실살리실산, 설파살라진 및 올살라진을 포함하는 살리실산 유도체; 아세트아미노펜을 포함하는 파라아미노펜올 유도체; 인도메타신, 술린닥 및 에토돌락을 포함하는 인돌 및 인덴 아세트산; 톨메틴, 다이클로페낙 및 케토로락을 포함하는 헤테로아릴 아세트산; 메페나믹산 및 메클로페나믹산을 포함하는 안트라닐릭산(페나메이트); 옥시캄(파이록시캄, 테녹시캄) 및 파이라졸리딘디온(페닐부타존, 옥시펜타타존)을 포함하는 에놀릭산; 및 나부메톤을 포함하는 알카논.
NSAIDs의 보다 상세한 기술은 본 발명에서 사용한 약물 내에 포함될 것이며, 통풍 치료에 있어서 진통-해열제의 및 항염증성 신분 및 약물(Goodman & Gilman's The Pharmacological Basis of Therapeutics, 617-57)(Perry B. Molinhoff and Raymond W. Ruddon, Eds., Ninth Edition, 1996) 및 Glen R. Hanson의 레밍턴에서의 진통, 해열 및 항-염증성 약물: The Science and Practice of Pharmacy Vol Ⅱ, 1196-1221(A. R. Gennaro, Ed. 1995)를 보라. 이 문헌들은 본 발명의 참고자료로 반영되었다.
어떤 구현예에서, 본 발명의 화합물들은 항편두통성 약물과의 조합으로 약제학적 제형 내에 제제화될 수 있다. 항편두통성 약물은 알피로프라이드(alpiropride), 다이하이드로에르고타민(dihydroergotamine), 돌라서트론(dolasetron), 에르고코닌(ergocornine), 에르고코니닌(ergocorninine), 에르고크립틴(ergocryptine), 에르고트(ergot), 에르고타민(ergotamine), 플루메드록손 아세테이트(flumedroxone acetate), 포나진(fonazine), 리수라이드(lisuride), 로메라진(lomerizine), 메티세르기드 옥세토론(methysergide oxetorone), 피조틸린(pizotyline) 및 이들의 혼합물을 포함하지만, 이에 한정되는 것은 아니다.
제토제와 같은 어떤 부작용의 가능성을 감소시킬 수 있는 다른 치료학적 약물을 보조제로 첨가할 수 있다. 적합한 제토제로는메토클로프로미드(metoclopromide), 돔페리돈(domperidone), 프로클로페라진(prochloperazine), 프로메타진(promethazine), 클로프로마진(chlopromazine), 트리메토벤즈아미드(trimethobenzamide), 온단세트론(ondansetron), 그라니세트론(granisetron), 하이드록시진(hydroxyzine), 아세틸로신 모노에탄올아민(acethyleucine monoethanolamine), 알리자프라이드(alizapride), 아자세트론(azasetron), 벤즈퀸아미드(benzquinamide), 바이에타노우틴(bietanautine), 브로모프라이드(bromopride), 부클리진(buclizine), 클레보프라이드(clebopride), 사이클리진(cyclizine), 다이멘하이드라이네이트(dimenhydrinate), 다이펜니돌(diphenidol), 돌라세트론(dolasetron), 메클리진(meclizine), 메탈라탈(methallatal), 메토피마진(metopimazine), 나빌론(nabilone), 옥시펀딜(oxyperndyl), 피파마진(pipamazine), 스코폴아민(scopolamine), 설피라이드(sulpiride), 테트라하이드로칸나비놀(tetrahydrocannabinols), 티에틸페라진(thiethylperazine), 티오프로페라진(thioproperazine), 트로피세트론(tropisetron) 및 이들의 혼합물을 포함하지만, 이에 한정되는 것은 아니다.
어떤 구현예에서, 본 발명의 화합물은 β-아드레날린성 차단제와 조합으로 약제학적 제형 내에 제제화될 수 있다. 적합한 β-아드레날린성 차단제로는 아세부톨올(acebutolol), 알푸레놀올(alprenolol), 아모술라볼(amosulabol), 아로티놀올(arotinolol), 아테놀올(atenolol), 베푸놀올(befunolol),베타솔올(betaxolol), 베반톨올(bevantolol), 비스오프롤올(bisoprolol), 보핀돌올(bopindolol), 부쿠몰올(bucumonol), 부페톨올(bufetolol), 부푸랄올(bufuralol), 부니트롤올(bunitrolol), 부푸란올올(bupranolol), 부티드린하이드로클로라이드(butidrine hydrochloride), 부토필올올(butofilolol), 카라졸올(carazolol), 카테올올(carteolol), 카베딜올(carvedilol), 셀리프롤올(celiprolol), 세타몰올(cetamolol), 클로란올올(cloranolol), 다일레발올(dilevalol), 에파놀올(epanolol), 에스몰올(esmolol), 인데놀올(indenolol), 라베탈올(labetalol), 레보부놀올(levobunolol), 메핀돌올(mepindolol), 메티프라놀올(metipranolol), 메토프롤올(metoprolol), 모프롤올(moprolol), 나돌올(nadolol), 나독솔올(nadoxolol), 네비발올(nevivalol), 니페날올(nifenalol), 니프라딜올(nipradilol), 옥스프레놀올(oxprenolol), 펜부톨올(penbutolol), 핀돌올(pindolol), 프락톨올(practolol), 프로네탈올(pronethalol), 프로프라놀올(propranolol), 소탈올(sotalol), 설피날올(sulfinalol), 탈리놀올(talinolol), 터타톨올(tertatolol), 틸리솔올(tilisolol), 티몰올(timolol), 톨리프롤올(toliprolol) 및 시벤놀올(xibenolol)을 포함하지만, 이에 한정되는 것은 아니다.
어떤 구현예에서, 본 발명의 화합물은 진경제(anticonvulsant)와 조합으로 약제학적 제형 내에 제제화될 수 있다. 적합한 진경제의 예로는, 아세틸페네투라이드(acetylpheneturide), 알부토인(albutoin), 알록시돈(aloxidone), 아미노글루테티마이드(aminoglutethimide), 4-amino-3-하이드록시부티릭산(4-amino-3-hydroxybutyric acid), 아트로락타마이드(atrolactamide), 베클아미드(beclamide), 부라메이트(buramate), 칼슘 브로마이드, 카바마제핀(carbamazepine), 신로마이드(cinromide), 클로메티아졸(clomethiazole), 클로나제팜(clonazepam), 데시메마이드(decimemide), 다이에타디온(diethadione), 다이메타디온(dimethadione), 독세나이트로인(doxenitroin), 에테로발브(eterobarb), 에타디온(ethadione), 에토수시마이드(ethosuximide), 에토토인(ethotoin), 펠바메이트(felbamate), 플루오레손(fluoresone), 가바펜틴(gabapentin), 5-하이드록시트립토판(5-hydroxytryptophan), 라모트리긴(lamotrigine), 마그네슘 브로마이드, 마그네슘 설페이트, 메페니토인(mephenytoin), 메포발비탈(mephobarbital), 메탈비탈(metharbital), 메테토인(methetoin), 메트수시마이드(methsuximide), 5-메틸-5-(3-페난트릴)-하이단토인(5-methyl-5-(3-phenanthryl)-hydantoin), 3-메틸-5-페닐하이단토인(3-methyl-5-phenylhydantoin), 날코발비탈(narcobarbital), 니메타제팜(nimetazepam), 니트라제팜(nitrazepam), 옥스카바제핀(oxcarbazepine), 파라메타디온(paramethadione), 페나세마이드(pheuacemide), 페네탈피탈(phenetharbital), 페네투라이드(pheneturide), 페노발비탈(phenobarbital), 펜수시마이드(phensuximide), 페닐메틸발비투릭산(phenylmethylbarbituric acid), 페니토인(phenytoin), 페테닐레이트 소듐(phethenylate sodium), 포타슘 브로마이드, 프레가발린(pregabaline), 프리미돈(primidone), 프로가바이드(progabide), 소듐 브로마이드,솔라늄(solanum), 스토론티윰 브로마이드(strontium bromide), 수클로페나이드(suclofenide), 설티암(sulthiame), 테트란토인(tetrantoin), 티아가빈(tiagabine), 토피라메이트(topiramate), 트리메타디온(trimethadione), 발프록익 산(valproic acid), 발프로마이드(valpromide), 비가바트린(vigabatrin) 및 조니사마이드(zonisamide)를 포함하지만, 이에 한정되는 것은 아니다.
어떤 구현예에서, 본 발명의 화합물은 항울약(antidepressant)과의 조합으로 약제학적 제형 내에 제제화될 수 있다. 적합한 항울약의 예로는, 비네달린(binedaline), 카로사존(caroxazone), 시탈프람(citalpram), 다이메타잔(dimethazan), 펜카민(fencamine), 인달핀(indalpine), 인델록사진 하이드로클로라이드(indeloxazine hydrochloride), 네포팜(nefopam), 노미펜신(nomifensine), 옥시트립탄(oxitriptan), 옥시펄틴(oxypertine), 파록세틴(paroxetine), 설트랄린(sertraline), 티아제심(thazesim), 트라조돈(trazodone), 벤모신(benmoxine), 이프로클로자이드(iproclozide), 이프로니아자이드(iproniazid), 아이소카르복사자이드(isocarboxazid), 니알아미드(nialamide), 옥타모신(octamoxin), 페넬진(phenelzine), 코티닌(cotinine), 롤리시프린(rolicyprine) , 롤리프람(rolipram), 마프로틸린(maprotiline), 메트랄린돌(metralindole), 미안세린(mianserin), 멀타제핀(mirtazepine) , 아디나졸람(adinazolam), 아미트립틸린(amitriptyline), 아미트립틸린옥사이드(amitriptylinoxide), 아목사핀(amoxapine), 부트립틸린(butriptyline), 클로미프라민(clomipramine),데멕십틸린(demexiptiline), 데시프라민(desipramine), 다이벤제핀(dibenzepin), 다이메타크린(dimetacrine), 도티에핀(dothiepin), 도세핀(doxepin), 플루아시진(fluacizine), 이미프라민(imipramine), 이미프라민 N-옥사이드(imipramine N-oxide), 이프린돌(iprindole), 로페프라민(lofepramine), 멜리트라센(melitracen), 메타프라민(metapramine), 놀트립틸린(nortriptyline), 녹십틸린(noxiptilin), 오피프라몰(opipramol), 피조틸린(pizotyline), 프로피제핀(propizepine), 프로트립틸린(ptotriptyline), 퀴누프라민(quinupramine), 티아넵틴(tianeptine), 트리미프라민(trimipramine), 아드라피닐(adrafinil), 베낙티진(benactyzine), 부프로피온(bupropion), 부타세틴(butacetin) , 다이옥사드롤(dioxadrol), 둘록세틴(duloxetine), 에토페리돈(etoperidone), 페발바메이트(febarbamate), 페모세틴(femoxetine), 펜펜타디올(fenpentadiol), 플루옥세틴(fluoxetine), 플루복사민(fluvoxamine), 헤마토폴피린(hematoporphyrin), 하이퍼리신(hypericin), 레보파세토페란(levophacetoperane), 메디포사민(medifoxamine), 밀나시프란(milnacipran), 미나프린(minaprine), 모클로베마이드(moclobemide), 네파조돈(nefazodone), 옥사플로잔(oxaflozane), 피베랄린(piberaline), 프롤린탄(prolintane), 파이리석시데아놀(pyrisuccideanol), 리탄세린(ritanserin), 로신돌(roxindole), 루비듐 클로라이드, 설피라이드(sulpiride), 탄도스파이론(tandospirone), 토잘리논(thozalinone), 토페나신(tofenacin), 톨로사톤(toloxatone), 트라닐시프로민(tranylcypromine), L-트립토판(L-tryptophan), 벤라파신(venlafaxine), 빌록사진(viloxazine) 및 지멜딘(zimeldine)을 포함하지만, 이에 한정되는 것은 아니다.
어떤 구현예에서, 본 발명의 화합물은 Ca2+- 채널 차단제와의 조합으로 약학적 제형 내에 제제화될 수 있다. 적합한 Ca2+- 채널 차단제로는 베프리딜(bepridil), 클레티아젬(cletiazem), 딜티아젬(diltiazem), 펜딜린(fendiline), 갈롭파밀(gallopamil), 미베프라딜(mebefradil), 프레닐아민(prenylamine), 세모티아딜(semotiadil), 테로딜린(terodiline), 베라파밀(verapamil), 아믈로디핀(amlodipine), 아라니디핀(aranidipine), 바니디핀(barnidipine), 베니디핀(benidipine), 실니디핀(cilnidipine), 에포니디핀(efonidipine), 엘고디핀(elgodipine), 펠로디핀(felodipine), 이스라디핀(isradipine), 라시디핀(lacidipine), 러카니디핀(lercanidipine), 메니디핀(manidipine), 니카디핀(nicardipine), 니페디핀(nifedipine), 닐바디핀(nilvadipine), 니모디핀(nimodipine), 니솔디핀(nisoldipine), 니트렌디핀(nitrendipine), 신나리진(cinnarizine), 플루나리진(flunarizine), 리도플라진(lidoflazine), 로머리진(lomerizine), 벤사이클란(bencyclane), 에타페논(etafenone), 판토파론(fantofarone) 및 퍼헥실린(perhexiline)을 포함하지만, 이에 한정되는 것은 아니다.
어떤 구현예에서, 본 발명의 화합물들은 항암제와의 조합으로 약제학적 제형내에 제제화될 수 있을 것이다. 적합한 항암제로는 아시비신(acivicin); 아클라루비신(aclarubicin); 아코다졸 하이드로클로라이드(acodazole hydrochloride); 아크로닌(acronine); 아도젤레신(adozelesin); 알데스로킨(aldesleukin); 알트레타민(altretamine); 암보마이신(ambomycin); 아메탄트론 아세테이트(ametantron acetate); 아미노글루테티마이드(aminoglutethimide); 암사크린(amsacrine); 아나스트로졸(anastrozole); 안트라마이신(anthramycin); 아스파라거스; 아스페린(asperlin); 아자시티딘(azacitidine); 아제테파(azetepa); 아조토마이신(azotomycin); 바티마스타트(batimastat); 벤조데파(benzodepa); 바이칼루타마이드(bicalutamide); 바이산트렌 하이드로클로라이드(bisantrene hydrochloride); 비스나파이드 다이메실레이트(bisnafide dimesylate); 바이젤레신(bizelesin); 블레오마이신 설페이트(bleomycin sulfate); 브레퀴나 소듐(brequinar sodium); 브로피리민(propirimine); 부설판(busulfan); 칵티노마이신(cactinomycin); 칼루스테론(calusterone); 카라세마이드(caracemide); 칼베타이머(carbetimer); 카보플라틴(carboplatin); 카무스틴(carmustine); 카루비신 하이드로클로라이드(carubicin hydrochloride); 카르젤레신(carzelesin); 세데핀골(cedefingol); 클로람부실(chlorambucil); 시롤레마이신(cirolemycin); 시스플라틴(cisplatin); 클라드리빈(cladribine); 크리스나톨 메실레이트(crisnatol mesylate); 사이클로포스파미드(cyclophosphamide); 시타라빈(cytarabine); 다칼바진(dacarbazine); 닥티노마이신(dactinomycin); 도우노루비신 하이드로클로라이드(daunorubicin hydrochloride); 데시타빈(decitabine), 덱소마플라틴(dexormaplatin); 데자구아닌(dezaguanine); 데자구아닌 메실레이트(dezaguanine mesylate); 다이아지퀴온(diaziquone);도세탁셀(docetaxel); 독소루비신(doxorubicin); 독소루비신 하이드로클로라이드(doxorubicin hydrochloride); 드롤로시펜(droloxifene); 드롤로시펜 시트레이트(droloxifene citrate); 드로모스타놀온 프로피오네이트(dromostanolone propionate); 두아조마이신(duazomycin); 에다트레세이트(edatrexate); 에플로니틴 하이드로클로라이드(eflornithine hydrochloride); 엘사미트루신(elsamitrucin); 엔롭라틴(enloplatin); 엔프로메이트(enpromate); 에피프로피딘(epipropidine); 에피루비신 하이드로클로라이드(epirubicin hydrochloride); 에르브로졸(erbulozole); 에소루비신 하이드로클로라이드(esorubicin hydrochloride); 에스트라무스틴(estramustine); 에스트라무스틴 포스페이트 소듐(estramustine phosphate sodium); 에타니다졸(etanidazole); 에토포사이드(etoposide); 에토포사이드 포스페이트(etoposide phosphate); 에토프린(etoprine); 파드라졸 하이드로클로라이드(fadrazole hydrochloride); 파자라빈(fazarabine); 펜레티나이드(fenretinide); 플록수리딘(floxuridine); 플루다라빈 포스페이트(fludarabine phosphate); 플루오로우라실(fluorouracil); 플루오로시타빈(fluorocitabine); 포스퀴돈(fosquidone); 포스트리에신 소듐(fostriecin sodium); 겜시타빈(gemcitabine); 겜시타빈 하이드로클로라이드(gemcitabine hydrochloride); 하이드록시우레아; 이다루비신 하이드로클로라이드(idarubicin hydrochloride); 이포스프아미드(ifosfamide); 일모포신(ilmofosine); 인터로킨 Ⅱ(interleukin Ⅱ)(재조합형 interleukin Ⅱ 또는 r ⅠL2를 포함하는), 인터페론알파-2a(interferon alfa-2a); 인터페론 알파-2b(interferon alfa-2b); 인터페론 알파-n1(interferon alfa-n1), 인터페론 알파-n3(interferon alfa-n3); 인터페론 베타-Ⅰa(interferon beta-Ⅰa); 인터페론 감마-Ⅰb(interferon gamma-Ⅰb); 이프로플라틴(iproplatin); 이리노테칸 하이드로클로라이드(irinotecan hydrochloride); 란레오타이드 아세테이트(lanreotide acetate); 레트로졸(letrozole); 로프로라이드 아세테이트(leuprolide acetate); 리아로졸 하이드로클로라이드(liarazole hydrochloride); 로메트렉솔 소듐(lometrexol sodium); 로무스틴(lomustine); 로소잔트론 하이드로클로라이드(losoxantrone hydrochloride); 마조프로콜(masoprocol); 메이탄신(maytansine); 메클로레타민 하이드로클로라이드(mechlorethamine hydrochloride); 메제스토롤 아세테이트(megestrol acetate); 멜렌제스트롤 아세테이트(melengestrol acetate); 멜파란(melphalan); 메노가릴(menogaril); 머켑토푸린(mercaptopurine); 메토트렉세이트(methotrexate); 메토트렉세이트 소듐(methotrexate sodium); 메토프린(metoprine); 메투레데파(meturedepa); 미틴도마이드(mitindomide); 미토카신(mitocarcin); 미토크로민(mitocromin); 미토길린(mitogillin); 미토말신(mitomalcin); 미토마이신(mitomycin); 미토스퍼(mitosper); 미토탄(mitotane); 미토잔트론 하이드로클로라이드(mitoxantrone hydrochloride); 미코페놀릭 산(mycophenolic acid); 노코다졸(nocodazole); 노갈라마이신(nogalamycin); 올마플라틴(ormaplatin); 옥시수란(oxisuran); 파클리타셀(paclitaxel); 페가스파가스(pegaspargase); 펠리오마이신(peliomycin); 펜타무스틴(pentamustine); 페플로마이신 설페이트(peplomycin sulfate); 퍼포스파미드(perfosfamide); 피포브로만(pipobroman); 피포설판(piposulfan); 피로잔트론 하이드로클로라이드(piroxantrone hydrochloride); 플리카마이신(plicamycin); 플로메스탄(plomestane); 폴피머 소듐(porfimer sodium); 폴피로마이신(profiromycin); 프레드니무스틴(prednimustine); 프로카바진 하이드로클로라이드(procarbazine hydrochloride); 푸로마이신(puromycin); 푸로마이신 하이드로클로라이드(puromycin hydrochloride); 파이라조푸린(pyrazofurin); 리보프린(riboprine); 로글레티마이드(rogletimide); 사핀골(safingol); 사핀골 하이드로클로라이드(safingol hydrochloride); 세무스틴(semustine); 심트라젠(simtrazene); 스파포세이트 소듐(sparfosate sodium); 스파소마이신(sparsomycin); 스파이로게르마늄 하이드로크로라이드(spirogermanium hydrochloride); 스파이로무스틴(spiromustine); 스파이로플라틴(spiroplatin); 스트렙토니그린(streptonigrin); 스테렙토조신(streptozocin); 술로페누르(sulofenur); 탈리소마이신(talisomycin); 테코갈란 소듐(tecogalan sodium); 테가푸르(tegafur); 텔로잔트론 하이드로클로라이드(teloxantron hydrochloride); 테모포핀(temoporfin); 테니포사이드(teniposide); 테록시론(teroxirone); 테스토락톤(testolactone); 티아미프린(thiamiprine); 티오구아닌(thioguanine); 티오테파(thiotepa); 티아조푸린(tiazofurin); 티라파자민(tirapazamine); 토레미펜 시트레이트(toremifene citrate); 트레스톨론아세테이트(trestolone actate); 트리시리빈 포스페이트(triciribine phosphate); 트리메트렉세이트(trimetrexate); 트리메트렉세이트 글루쿠로네이트(trimetrexate glucuronate); 트립토렐린(triptorelin); 투불로졸 하이드로클로라이드(tubulozole hydrochloride); 우라실 머스타드(uracil mustard); 우레데파(uredepa); 바프레오타이드(vapreotide); 벌테포핀(verteporfin); 빈블라스틴 설페이트(vinblastine sulfate); 빈크리스틴 설페이트(vincristine sulfate); 빈데신(vindesine); 빈데신 설페이트(vindesine sulfate); 비네피딘 설페이트(vinepidine sulfate); 빈글리시네이트 설페이트(vinglycinate sulfate); 빈루오로신 설페이트(vinleurosine sulfate); 빈오렐빈 탈트레이트(vinorelbine tartrate), 빈로시딘 설페이트(vinrosidine sulfate); 빈졸리딘 설페이트(vinsolidine sulfate); 보로졸(vorozole); 제니플라틴(zeniplatin); 지노스타틴(zinostatin); 조루비신 하이드로클로라이드(zorubicin hydrochloride)를 포함하지만, 이에 한정되는 것은 아니다.
다른 항암제로는 20-에피-1,25다이하이드록시비타민 D3; 5-에티닐우라실; 아비라테론(abiraterone); 아클라루비신(aclarubicin); 아실풀벤(acylfulvene); 아데시펜올(adecypenol); 아도제레신(adozelesin); 알데스로킨(aldesleukin); ALL-TK 길항근; 알트레타민(altretamine); 암바무스틴(ambamustine); 아미독스(amidox); 아미포스틴(amifostine); 아미노레블리닉 산(aminolevulinic acid); 암루비신(amrubicin); 암사크린(amsacrine); 아나그레라이드(anagrelide); 아나스트로졸(anastrozole); 안드로그래폴라이드(andrographolide); 안기오제니시스 억제제 (angiogenesis inhibitors); 길항근 D; 길항근 G; 안타렐릭스(antarelix); 항-돌살라이징 형태성 단백질-1(antidorsalizing morphogenetic protein-1); 항안드로겐(antiandrogen); 전립선암 악성종양(prostatic carcinoma); 항에스토로겐(antiestrogen); 항종양(antineoplaston); 항감각성 올리고뉴클레오티드(antisense oligonucleotide); 아피디콜린 글리시네이트(aphidicolin glycinate); 고사 유전자 조절제(apoptosis gene modulators); 고사 조절제(apoptosis regulator); 아푸리닉산(apurinic acid); ara-CDP-DL-PTBA; 알기닌 디아미나제(arginine deaminase); 오술라크린(asulacrine); 아타메스탄(atamestane); 아트리무스틴(atrimustine); 엑시나스타틴 1(axinastatin 1); 엑시나스타틴 2(axinastatin 2); 엑시나스타틴 3(axinastatin 3); 아자세트론(azasetron); 아자토신(azatoxin); 아자티로신(azatyrosine); 바카틴 Ⅲ 유도체(baccatin Ⅲ derivatives); 발라놀(balanol); 바티마스타트(batimastat); BCR/ABL 길항근; 벤조클로린(benzochlorine); 벤조일스타우로스포린(benzoylstaurosporine); 베타 락탐 유도체(beta lactam derivatives); 베타-알레틴(beta-alethine); 베타클라마이신 B(betaclamycin B); 베투리닉산(betulinic acid); bFGF 억제제; 바이칼루타마이드(bicalutamide); 비스안트렌(bisantrene); 비스아지리디닐스페르민(bisaziridinylspermine); 비스나파이드(bisnafide); 비스트라텐 A(bistratene A); 비제레신(bizelesin); 브레플레이트(breflate); 브로피리민(propirimine); 부도티탄(budotitane); 부티오닌 설폭시민(buthionine sulfoximine); 칼시포트리올(calcipotriol); 칼포스틴C(calphostin C); 캠프토테신 유도체(camptothecin derivatives); 카나리폭스 IL-2(canarypox IL-2); 카페시타빈(capecitabine); 카르복사마이드-아미노-트리아졸(carboxamide-amino-triazole); 카르복시아미도트리아졸(carboxyamidotriazole); CaRest M3; CARN 700; 연골 유도된 억제제(cartilage derived inhibitor); 카젤레신(carzelesin); 카세인 키나제 억제제(casein kinase inhibitors, ICOS); 카스타노스페르민(castanospermine); 세크로핀 B(cecropin B); 세트로렐릭스(cetrorelix); 클로린스(chlorlns); 클로로퀴녹살린 설폰아미드(chloroquinoxaline sulfonamide); 시카프로스트(cicaprost), 시스-폴피린; 클라드리빈(cladribine); 클로미펜 유사체(clomifene analogues); 클로트리마졸(clotrimazole); 콜리스마이신 A(collismycin A); 콜리스마이신 B(collismycin B); 컴브레타스타틴 A4(combretastatin A4); 컴브레타스타틴 유사체(combretastatin analogues); 코나게닌(conagenin); 크램베스시딘 816(crambescidin 816); 크리스나톨(crisnatol); 크립토피신 8(cryptophycin 8); 크립토피신 A 유도체; 쿠라신 A(curacin A); 사이클로펜탄트라퀴논(cyclopentanthraquinone); 사이클로플라탐(cycloplatam); 사이페마이신(cypemycin); 시타라빈 옥포스페이트(cytarabine ocfosfate); 시톨리틱 인자(cytolytic factor); 시토스타틴(cytostatin); 다클릭시맵(dacliximab); 데시타빈(decitabine); 디하이드로디뎀닌 B(dehydrodidemnin B); 데스로레린(deslorelin); 덱사메타손(dexamethasone); 덱시포스프아마이드(dexifosfamide); 덱스트라조산(dextrazoxane);덱스버라파밀(dexverapamil); 다이아지퀴온(diaziquone); 디뎀닌 B(didemnin B); 디독스(didox); 다이에틸놀스퍼민(diethylnorspermine); 다이하이드로-5-아자시티딘(dihydro-5-azacytidine); 다이하이드로타솔(dihydrotaxol), 9; -다이옥사마이신(9-dioxamycin); 다이페닐 스파이로무스틴(diphenyl spiromustine); 도케타셀(docetaxel); 도코산올(docosanol); 도라세트론(dolasetron); 도시플루리딘(doxifluridine); 드롤로시펜(droloxifene); 드로나비놀(dronabinol); 두오카마이신 SA(duocamycin SA); 에브세렌(ebselen); 에코무스틴(ecomustine); 에델포신(edelfosine); 에드레콜로맵(edrecolomab); 에플로니틴(eflornithine); 엘레멘(elemene); 에미테푸르(emitefur); 에피루비신(epirubicin); 에프리스테라이드(epristeride); 에스트라무스틴 유사체(estramustine analogue); 에스트로겐 작용약(estrogen agonist); 에스트로겐 길항근(estrogen antagonist); 에타니다졸(etanidazole); 에토포사이드 포스페이트(etoposide phosphate); 엑세메스탄(exemestane); 파드로졸(fadrozole), 파자라빈(fazarabine); 펜러티나이드(fenretinide); 필그라스팀(filgrastim); 피나스테라이드(finasteride); 플리보피리돌(flavopiridol); 플레젤라스틴(flexelastine); 플루아스테론(fluasterone); 플루다라빈(fludarabine); 플루오로다우노우니신 하이드로클로라이드(fluorodauuorunicin hydrochloride); 포페니멕스(forfenimex); 포멕스탄(formestane); 포스트리에신(fostriecin), 포테무스틴(fotemustine); 가돌리늄 텍사피린(gadolinium texaphyrin); 갈륨 나이트레이트(gallium nitrate); 갈로시타빈(galocitabine); 가닐렐릭스(ganirelix); 젤라티나제 억제제(gelatinaseinhibitors); 겜시타빈(gemcitabine); 글루타티온 억제제(glutathione inhibitors); 헵설팜(hepsulfam); 헤레구린(heregulin); 헥사메틸렌 비스아세트아마이드(hexamethylene bisacetamide); 하이퍼리신(hypericin); 이반드로닉 산(ibandronic acid); 아이다루비신(idarubicin); 아이독시펜(idoxifene); 아이드라만톤(idramantone); 일모포신(ilmofosine); 일로마스테이트(ilomastat); 이미다조아크리돈(imidazoacridones); 이미퀴모드(imiquimod); 이뮤노스티물란트 펩타이드(immunostimulant peptides); 인슐린과 같은 성장 인자-1 수용체 억제제, 인터페론 작용약, 인터페론, 인터루킨(interleukin); 이이오벤구안(iobenguane); 요오도독소루비신(iododoxorubicin); 이포미아놀(ipomeanol); 4-; 이로플랙트(iroplact); 아이르소글라딘(irsogladine); 아이소벤가졸(isobengazole); 아이소호모할리콘드린 B(isohomogalicondrin B); 이타세트론(itasetron); 자스플라키놀라이드(jasplakinolide); 카할라라이드 F(kahalalide F); 라멜라린-N트리아세테이트(lamellarin-N triacetate); 란레오타이드(lanreotide); 레이나마이신(leinamycin); 레노그라스팀(lenograstim); 렌티난 설페이트(lentinan sulfate); 렙톨스타틴(leptolstatin); 레트로졸(letrozole); 루케미아 억제 인자(leukemia inhibiting factor); 백혈구 알파 인터페론(leukocyte alpha interferon); 루프롤라이드+에스트로겐+프로게스테론;(leuprolide+estrogen+progesterone); 루프로렐린(leuprorelin); 레바미솔(levamisole); 리아라졸(liarazole); 직쇄상 폴리아민 유사체(linear polyamine analogue); 리포필릭 이당 펩타이드(lipophilic disaccharide peptide); 리포필릭 플래티늄 화합물(lipophilic platinumcompounds); 리소클린아마이드 7(lissoclinamide 7); 로바플라틴(lobaplatin); 롬브리신(lombricine); 로메트렉솔(lometrexol); 로니드아민(lonidamine); 로소잔트론(losoxantrone); 로바스타틴(lovastatin); 록소리빈(loxoribine); 루르토테칸(lurtotecan); 루테티움 텍사피린(lutetium texaphyrin); 리소필린(lysofylline); 리틱 펩타이드(lytic peptide); 마이탄신(maitansine); 만노스타틴 A(mannostatin A); 마리마스타트(marimastat); 마소프로콜(masoprocol); 마스핀(maspin); 메트릴리신 억제제(matrilysin inhibitors); 메트리스 메탈로프로티나제 억제제(matrix metalloproteinase inhibitors); 메노가릴(menogaril); 멀바론(merbarone); 메테럴린(meterelin); 메티오니나제(methioninase); 메토클로프르아마이드(metoclopramide); MIF 억제제; 미페프리스톤(mifepristone); 밀테포신(miltefosine); 미리모스팀(mirimostim); 잘못 짝지은 두 가닥의 RNA(mismatch double stranded RNA); 미토구아존(mitoguazone); 미토락톨(mitolactol); 미토마이신 유사체(mitomycin analogues); 미토나파이드(mitonafide); 미토토신 섬유아세포 성장 인자-사포린(mitotoxin fibroblast growth factor-saporin); 미토잔트론(mitoxantrone); 모파로텐(mofarotene); 몰그라모스팀(molgramostim); 단일세포에서 유래하는 세포인에서 만들어진 항체(monoclonal antibody); 인간의 융모막성 생식선 자극 호르몬(human chorionic gonadotrophin); 모노포스포릴 리피드 A+미오박테리움 세포 벽 sk(monophosphoryl lipid A + myobacterium cell wall sk); 모피다몰(mopidamol); 복합 약물 저항 유전자 억제제(multiple drug resistancegene inhibitor); 복합 암 억제유전자 1-기초한 치료(multiple tumor suppressor 1-based therapy); 머스타드 항암제(mustard anticancer agent), 마이카펄옥사이드 B(mycaperoxide B); 마이코박테리아 세포 벽 추출물(mycobacterial cell wall extract); 마이리아포론(myriaporone); N-아세틸디날린(N-zcetyldinaline); N-치환된 벤즈아마이드(N-substituted benzamide); 나파렐린(nafarelin); 나그레스팁(nagrestip); 날록손+펜타조신; 나파빈(napavin); 나프터핀(naphterpin); 나토그라스팀(nartograstim); 네다플라틴(nedaplatin); 네모루비신(nemorubicin); 네리드로닉산(neridronic acid); 중성 엔도펩티다제(neutral endopeptidase); 니루타마이드(nilutamide); 니사마이신(nisamycin); 나이트릭 옥사이드 조절제; 나이트로옥사이드 항산화제; 니트루린(nitrullyn); 06-벤질구아닌(06-benzylguanine); 옥트레오타이드(octreotide); 오키케논(okicenone); 올리고뉴클레오티드(oligonucleotide); 오나프리스톤(onapristone); 온단세트론(ondansetron); 오라신; 경구용 시토킨 유도물질(oral cytokine inducer); 올마플라틴(ormaplatin); 오사테론(osaterone); 옥사리플라틴(oxaliplatin); 옥사우노마이신(oxaunomycin); 파클리타셀(paclitaxel); 파클리타셀 유사체((paclitaxel analogues); 파클리타셀 유도체(paclitaxel derivatives); 팔라우아민(palauamine); 팔미토일리조신(palmitoylrhizoxin); 파미드록닉 산(pamidronic acid); 파낙시트리올(panaxytriol); 파노미펜(panomifene); 파라박틴(parabactin);파젤립틴(pazelliptine); 페가스파가스(pegaspargase); 펠데신(peldesin); 펜토산 폴리설페이트 소듐(pentosan polysulfate sodium); 펜토스타틴(pentostatin); 펜트로졸(pentrozole); 퍼플루브론(perflubron); 퍼포스프아마이드(perfosfamide); 페릴릴 알콜(perillyl alcohol); 페나지노마이신(phenazinomycin); 페닐아세테이트(phenylacetate); 포스파타제 억제제(phosphatase inhibitors); 피시반닐(picibanil); 필로카핀 하이드로클로라이드(pilocarpine hydrochloride); 피라루비신(pirarubicin); 피리트렉심(piritrexim); 플라세틴 A(placetin A); 플라세틴 B(plasetin B); 플라스미노겐 활성 억제제(plasminogen activator inhibitor); 플래티늄 복합체(platinum complex); 플레티늄 화합물; 플래티늄-트리아민 복합체; 폴퍼머 소듐(profimer sodium); 폴피로마이신(porfiromycin); 프레드니손(prednisone); 프로필 비스-아크리돈(propyl bis-acridone); 프로스타글란딘 J2(prostaglandin J2); 프로티아좀 억제제(proteasome inhibitor); 프로틴-A 기초한 면역 조절제(protein A-based immune modulator); 프로틴 키나제 C 억제제(protein kinase C inhibitor); 마이크로알갈(microalgal); 프로틴 티로신 포스파타제 억제제(protein tyrosine phosphatase inhibitors); 푸린 뉴클레오사이드 포스포릴라제 억제제(purine nucleoside phosphorylase inhibitors); 풀푸린(purpurins); 파이라졸로아크리딘(pyrazoloacridine); 피리독실레이티드 헤모글로빈 폴리옥시에틸렌 결합(pyridoxylated hemoglobin polyoxyethylene conjugate); 래프 길항근(raf antagonist); 랄티트렉세드(raltitrexed); 라모세트론(ramosetron); 라스 파네실 프로틴 전이효소 억제제(ras farnesyl proteintransferase inhibitors); ras 억제제, ras-GAP 억제제; 레텔립틴 디메틸레이티드(retelliptine demethylated); 레늄 Re 186 에티드로네이트(rhenium Re 186 etidronate); 리조신(rhizoxin); 리보짐(ribozyme); RⅡ 레틴아미드; 로글레티미드(rogletimide); 로히투킨(rohitukine); 로머타이드(romurtide); 로퀴니멕스(roquinimex); 루비기논 B1(rubiginone B1); 루복실(ruboxyl); 사핀골(safingol); 세인토핀(saintopin); SarCNU; 살코피톨 A(sarcophytol A); 살그라모스팀(sargramostim); Sdi 1 미메틱스(Sdi 1 mimetices); 세무스틴(semustine); 노쇠 유도 억제제 1(senescene derived inhibitor 1); 감각 올리고뉴클레오티드(sense oligonucleotide); 신호 형질도입 억제제(signal trnasduction inhibitor); 신호 형질전환 조절제((signal trnasduction modulators); 신호 사슬 항원 결합 단백질(signal chain antigen binding protein); 시조피란(sizofiran); 소부조산(sobuzoxane); 소듐 보로캡테이트(sodium borocaptate); 소듐 페닐아세테이트(sodium phenylacetate), 솔베롤(solverol); 소마토메딘 결합 프로틴(somatomedin binding protein); 소널민(sonermin); 스파포식산(sparfosic acid); 스피카마이신 D(spicamycin D); 스파이로무스틴(spiromustine); 스플레노펜틴(splenopentin); 스폰기스타틴 1(spongistatin 1); 스쿠알아민(squalamine); 줄기 세포 억제제(stem cell inhibitors); 줄기 세포 분할 억제제; 스티피아마이드(stipiamide); 스트로멜리신 억제제(stromelysin inhibitors); 설피노신(sulfinosine); 초활성 혈관작용성의 장펩타이드 길항근(superactive vasoactive intestinal peptide antagonist); 수라디스타(suradista); 수라민(suramin); 스와인소닌(swainsonine); 합성 글루코사미노글리칸스(synthetic glycosaminoglycans); 탈리무스틴(tallimustine); 타목시펜 메티오다이드(tamoxifen methiodide); 토우로무스틴(tauromustine); 타자로텐(tazarotene); 테코갈란 소듐(tecogalan sodium); 테가푸르(tegafur); 텔루라피릴륨(tellurapyrylium); 텔로머라제 억제제(telomerase inhibitors); 테모폴핀(temoporfin); 테모졸로마이드(temozolomide); 테니포사이드(teniposide); 테트라클로로데카옥사이드; 테트라조민(tetrazomine); 탈리블라스틴(thaliblastine); 티오코랄린(thiocoraline); 트롬보포이에틴(thrombopoietin); 트롬보포이에틴 미메틱(thrombopoietin mimetic); 티말파신(thymalfasin); 티모포이에틴 수용체 작용약; 티모트리난; 티로이드 자극 호르몬; 틴 에틸 에티오풀푸린(tin ethyl etiopurpurin); 티라파자민(tirapazamine); 티탄노젠 바이클로라이드(titanocene bichloride); 톱센틴(topsentin); 토레미펜(toremifene); 토티포텐트 줄기 세포 인자(totipotent stem cell factor); 변형 억제제; 트레티노인(tretinoin); 트리아세틸우리딘(triacetyluridine); 트리시리빈(triciribine); 트리메트렉세이트(trimetrexate); 트립토렐린(triptorelin); 트로피세트론(tropisetron); 투로스테라이드(turosteride); 티로신 키나제 억제제; 티르포스틴(tyrphostin); UBC 억제제; 우베니멕스(ubenimex); 비뇨생식기의 공동-유도된 성장 억제 인자; 유로키나제 수용체 길항근; 바프레오타이드(vapreotide); 바리오린 B(variolin B); 벡터 시스템; 적혈구 유전자 치료; 벌라레졸(velaresol); 베라민(veramine); 베르딘(verdine); 베르테폴핀(verteporfin);비놀렐빈(vinorelbine); 빈잘틴(vinxaltine); 비타신(vitaxin); 보로졸(vorozole); 자노테론(zanoteron); 제니플라틴(zeniplatin); 질라스코브(zilascorb), 및 지노스타틴 스티말라머(zinostatin stimalamer)을 포함하지만, 이에 한정되는 것은 아니다.
본 발명의 화합물은 다른 치료 약물과 추가로, 보다 바람직하기로는 상승작용을 하는 역할을 수행한다. 바람직한 구현예에서, 본 발명의 화합물을 포함하는 조성물은 다른 치료 약물의 투여와 동시에 투여되는 바, 다른 치료 약물은 동일한 조성의 일부 또는 본 발명의 화합물을 포함하는 다른 조성의 약물을 의미한다. 다른 구현예에서, 본 발명을 포함하는 조성은 다른 치료 약물의 투여에 이어서 또는 그 이전에 투여되는 것이다.
본 발명의 화합물을 경구로, 비경구로 또는 피부를 통하여 포유동물에게 투여될 때에는, 환자 몸무게 당 하루에 약 0.01 내지 3000mg/kg, 바람직하기로는 약 0.01 내지 1000mg/kg의 복용량으로 한번에 또는 나누어진 도스로 투여된다. 그러나, 치료되고자 하는 환자의 몸무게와 신체적인 조건(예를 들면, 간장이나 신장 기능), 환자의 고통에 따라, 증상의 정도에 따라, 투여 경로에 따라, 투여 주기의 횟수에 따라, 유독한 부작용의 존재 및 적용되는 특정의 화합물 등에 따라 달라질 수 있다.
본 발명의 화합물은 바람직하기로는 인간의 ORL-1 수용체의 결합 친화력 Ki이 500nM 또는 그 미만; 100nM 또는 그 미만; 50nM 또는 그 미만; 20nM 또는 그 미만 또는 5nm 또는 그 미만이다. 결합 친화력 Ki은 이 분양의 능숙한 기술자들은 하기에 기술된 것과 같이 인간의 오피오이드 수용체와 같은 수용체(ORL-1)에 발현하는 재조합된 HEK-293 세포로부터 멤브레인을 이용한 시험으로부터 측정할 수 있을 것이다.
다음의 실시예는 본 발명의 다양한 양상들을 기술한 것이다. 이들은 어떠한 방법으로든지 청구항을 한정하려는 의도로 해석되어서는 안 될 것이다.
실시예 1: 스피로사이클릭 헤드 그룹의 합성
[반응식 1]
공정:
-40℃에서 THF 중에서 새로이 제조된 LDA(1.1당량)의 용액에 THF 중의 상기 화합물1(1당량)의 용액을 첨가하였다. 반응 혼합물을 실온에서 따뜻하게 방치하면서 1시간 동안 교반하였다. -20℃에서 냉각한 후 THF 중의 벤조일 클로라이드(2, 1.2당량)를 점적하여 첨가하였다. -20℃에서 1시간 및 실온에서 16시간 동안 교반한 후, 반응 혼합물을 물에 부어 에틸 아세테이트로 추출하였다. 유기 추출물을 진한 암모늄 클로라이드, 소금물로 세척하고 MgSO4상에서 건조, 여과 및 용매를 증발시켜 원료 생성물3을 오일로써 얻고, 이를 정제과정 없이 다음 단계에 사용하였다.
1H-NMR(CDCl3): d 1.08(t,3H), 2.28(t,4H), 2.43(m,2H), 2.54(m,2H), 3.46(s,2H), 4.13(q,2H), 7.21-7.31(m,5H), 7.39(m,2H), 7.49(m,1H), 7.79(m,2H).
에탄올 중에서 상기 화합물3의 용액(1당량)에 하이드라진 하이드레이트(3당량)을 첨가하였다. 12시간 동안 환류한 후, 반응 혼합물을 실온에서 냉각하고 원료생성물을 여과하였다. 고체를 에탄올로부터 재결정하여 백색 고체로써 상기 화합물4를 얻었다.
1H-NMR(DMSO): d 1.67(d,2H), 2.23(dt,2H), 2.62(dd,2H), 2.83(dt,2H), 3.56(s,2H), 7.25(m,1H), 7.35(m,4H), 7.50(m,3H), 7.78(m,2H).
메탄올 중에서 상기 화합물4(1당량)과 Pd(OH)2(0.2당량)을 실온 및 수소압 50psi에서 20시간 동안 수소화하였다. 여과 및 증발시켜 원료생성물 5를 얻었다. 에탄올로부터 재결정하여 순수 화합물5를 백색 고체로써 얻었다.
1H-NMR(DMSO): d 1.50(d,2H), 2.12(m,2H), 2.73(m,2H), 3.28(m,2H), 7.45(m,3H), 7.86(d,2H).
실시예 2: 테일 그룹의 도입
테일 그룹을 다음 반응식 2의 공정에 따라서 헤드그룹에 도입하였다.
[반응식 2]
알킬레이션의 일반적인 공정:
디메틸포름아마이드 중의 아민(1당량)과 트리에틸아민(1당량)의 용액에 알킬브로마이드 또는 알킬 클로라이드 1당량을 한꺼번에 첨가하였다. 혼합물을 교반하고 80℃에서 밤샘 가열하였다. TLC로 반응의 완결을 확인하였다. 반응물을 물을 첨가하여 냉각시키고 1N NaOH로 pH 10이 되도록 하였다. 이 혼합물을 Et2O로 2번 추출하였다. 혼합된 유기 추출물을 포타슘 카보네이트 상에서 건조하고 용매를 증류시킨 다음, 크로마토그래피하여 순수 생성물을 얻었다.
환원성 아민화의 일반적인 공정:
메탄올 중의 케톤 또는 알데하이드(1당량), 아민(1당량) 및 아세트산(1당량)의 혼합액에 소듐 시아노보로하이드라이드(1.4당량)를 한꺼번에 첨가하였다. 혼합물을 실온에서 밤샘 교반하였다. TLC로 반응의 완결을 확인하였다. 반응물을 물을 첨가하여 냉각시키고 1N NaOH로 pH 10이 되도록 하였다. 이 혼합물을 Et2O로 2번 추출하였다. 혼합 유기 추출물을 포타슘 카보네이트 상에서 건조하고 용매는 증류시킨 다음, 크로마토그래피하여 순수 생성물을 얻었다.
다음 화합물들을 상기의 일반적인 공정을 이용하여 테일 그룹을 도입함으로써 제조하였다:
8-(벤질)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
MS: m/z 342.2(M+Na)
1H-NMR(DMSO): d 1.67(d,2H), 2.23(dt,2H), 2.62(dd,2H), 2.83(dt,2H), 3.56(s,2H), 7.25(m,1H), 7.35(m,4H), 7.50(m,3H), 7.78(m,2H).
8-[(나프트-2-일-메틸)]-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 97.7% MS: m/z 370.6(M+1)
1H-NMR(CDCl3): d 1.80(b,2H), 2.50(m,2H), 2.80(b,2H), 2.03(t,2H), 3.75(s,2H), 7.50(m,5H), 7.60(d,1H), 7.80(m,6H), 8.42(b,1H).
8-(p-페닐벤질)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 90.1%, MS: m/z 396.6(M+1)
1H-NMR(CDCl3): d 1.80(b,2H), 2.51(m,2H), 2.80(b,2H), 3.02(m,2H), 3.75(s,2H), 7.35-7.70(m,12H), 7.85(b,2H), 8.50(b,1H).
8-(10,11-디하이드로-5H-디벤조[a.d]-사이클로헵텐-5-일)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 444.2(M+Na)
1H-NMR(CDCl3): d 1.75(b,2H), 2.35(m,2H), 2.61(b,2H), 2,85(m,4H), 4.11(m,2H), 4.20(s,1H), 7.10-7.28(m,8H), 7.45(m,3H), 7.85(m,2H), 8.5(s,1H).
8-[4,4-비스(4-플루오로페닐)부틸]-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 96.9%, MS: m/z
1H-NMR(CDCl3): d 0.75-2.90(m,10H), 3.60(m,2H), 3.80(m,1H), 3.90(m,1H), 4.55(m,1H), 6.90-7.50(m,11H), 7.80(b,2H), 8.45(b,1H).
8-(3,3-비스(페닐)프로필)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 424.2(M+1)
1H-NMR(CDCl3): d 1.80(b,2H), 2.35(m,2H), 2.50(m,4H), 2.78(b,2H), 2.95(m,2H), 4.05(t,1H), 7.20(m,2H), 7.30(m,8H), 7.45(m,3H), 7.85(b,2H), 8.70(b,1H).
8-(p-벤질옥시벤질)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 97.6%, MS: m/z 426.2
1H-NMR(CDCl3): d 1.80(b,2H), 2.45(dt,2H), 2.80(b,2H), 2.95(m,2H), 3.60(s,2H), 5.10(s,2H), 6.95(d,2H), 7.30-7.50(m,10H), 7.88(m,2H), 8.71(s,1H).
8-(1,2,3,4-테트라하이드로-2-나프틸)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 95.3%, MS: m/z 360.2(M+1)
1H-NMR(CDCl3): d 1.85-1.90(m,3H), 2.42(b,1H), 2.85-3.15(m,6H), 3.20(b,2H), 3.40(m,2H), 3.75(m,1H), 7.10-7.20(m,4H), 7.50(m,3H), 8.00(d,2H).
8-(4-프로필사이클로헥실)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 354.2(M+1)
1H-NMR(CDCl3): d 1.95(t,3H), 1.35(m,6H), 1.60(m,2H), 1.80(m,3H), 1.95(d,4H), 2.25(d,1H), 3.05(t,3H), 3.30(d,2H), 3.8(q,2H), 7.50(t,1H), 7.60(m,2H), 8.00(d,2H)
8-(5-메틸헥스-2-일)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 328.2(M+1)
1H-NMR(CDCl3): d 0.9-1.65(m,12H), 2.00(bd,4H), 2.05-2.30(m,5H), 3.95(t,2H), 7.50(t,1H), 7.60(t,2H), 8.02(d,2H).
8-노보닐-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
MS: m/z 324.2(M+1)
1H-NMR(CDCl3): d 0.80-3.90(m,16H), 4.20(m,2H), 4.85(b,1H), 7.40-7.62(m,3H), 8.05(m,2H), 8.75(b,1H).
8-(데카하이드로-2-나프틸)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 366.2(M+1)
1H-NMR(CDCl3): d 0.95-2.15(m,17H), 2.30(m,1H), 3.10(m,3H), 3.35(m,2H), 3.95(m,2H), 7.55(t,1H), 7.65(t,2H), 8.02(d,2H).
8-(사이클로옥틸메틸)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 340.2(M+1)
1H-NMR(CDCl3): d 1.40-2.25(m,16H), 3.10(m,2H), 3.20(b,2H), 3.38(m,1H), 4.02(m,2H), 7.50(t,1H), 7.60(t,2H), 8.02(m,2H).
8-[4-(2-프로필)-사이클로헥실]-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 354.2(M+1)
1H-NMR(CDCl3): d 0.9(m,6H), 1.45-1.65(m,3H), 1.78(m,2H), 2.00(b,6H), 2.30(d,1H), 3,10(m,3H), 3.30(t,2H), 3.95(q,2H), 7.50(t,1H), 7.60(t,2H), 8.00(m,2H).
8-(1,3-디하이드로인덴-2-일)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 346.1(M+1)
1H-NMR(CDCl3): d 1.90-3.80(m,12H), 4.25(m,1H), 7.20-7.70(m,8H), 7.95(d,1H).
8-(사이클로옥틸메틸)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 92.9%, MS: m/z 354.6(M+1)
1H-NMR(MeOH): d 1.40-1.80(m,14H), 2.00(b,2H), 2.10(m,1H), 2.60(m,2H), 2.90(m,2H), 3.40(m,2H), 3.70(m,2H), 7.50(m,3H), 7.80.
8-(아세나프텐-9-일)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온
LC: 100%, MS: m/z 382.2(M+1)
1H-NMR(CDCl3): d 1.69(dd,1H), 1.72(dd,1H), 2.36-2.44(m,2H), 2.52-2.60(ddd,1H), 2.83(brd,1H), 3.17-3.24(m,1H), 3.30-3.44(m,2H), 3.60-3.65(m,1H), 5.01(dd,1H), 7.31(d,1H), 7.45-7.49(m,4H), 7.52-7.57(m,2H), 7.62-7.64(d,1H), 7.69-7.71(m,1H), 7.86-7.88(m,2H), 8.42(s,1H).
본 발명의 화학식 1 또는 3의 범주 내에서 다른 화합물을 유사한 기술에 의해 합성할 수 있다.
실시예 3
바람직한 화합물에 대한 ORL1 수용체에서 침해수용체 친화력(nociceptin affinity)을 다음과 같은 분석방법으로 얻었다:
인간 오피오이드 수용체-유사 수용체(ORL-1)(Recpetor Biology)로 표현되는 재조합형 HEK-293 세포로부터 멤브레인을 제조하되, 얼음으로 냉각된 저장 완충액(2.5mM MgCl2, 50mM HEPES, pH 7.4)(10㎖/10cm 디쉬) 내에서 세포를 용해시키고 조직 그라인더/테프론 막자로 균질화하여 멤브레인을 제조하였다. 멤브레인을 4℃에서 15분 동안 30,000×g으로 원심분리하여 수집하고 펠렛을 최종 농축물 1-3mg/㎖되도록 저장 완충액에 재현탁하였다. 단백질 농축액을 BioRad 단백질 분석 시약을 이용하여 대조구로서 소의 혈청 알부민으로써 측정하였다. OSL-1 수용체 멤브레인의 표본들을 -80℃에서 저장하였다.
함수적 SGTPgS 결합 분석을 다음과 같이 수행하였다. 얼음 상에서 ORL-1 멤브레인 단백질 0.066mg/㎖, 사포닌 10mg/㎖, GDP 3mM 및 [35S]GTPgS 0.20nM의 최종 농축물을 결합 완충액(100mM NaCl, 10mM MgCl2, 20mM HEPES, pH 7.4)에 순차적으로 첨가하여 ORL-1 멤브레인 수용액을 제조하였다. 제조된 멤브레인 용액(190㎖/웰)을 DMSO 중에서 제조된 효능제의 20배의 농축 저장 용액 10㎖를 함유하는 96-shallow well 폴리프로필렌 플레이트에 전사하였다. 플레이트를 진동시키면서 실온에서 30분 동안 배양하였다. 반응물을 96-웰 조직 수확기(Brandel)를 이용하여 96-웰 Unifilter GF/B 필터 플레이트(Packard) 상으로 고속 여과하여 측정하고 얼음 냉각된 결합 완충액(10mM NaH2PO4, 10mM Na2HPO4, pH7.4) 200㎖로 세 번 여과 세척하였다. 필터 플레이트를 이어서 2 내지 3시간 동안 50℃에서 건조하였다. 50 ㎖/웰 신틸레이션 칵테일(scintillation cocktail)(BeraScint; Wallac)을 첨가하고 플레이트를 Packard Top-Counts 내에서 1min/웰 동안 세었다.
데이터를 GraphPad PRISMO, v.3.0으로써 곡선형 함수를 이용하여 분석하여 그 결과를 다음 표 1에 나타내었다.
[표 1]
실시예 5
화합물들에 대한 μ 수용체에서 친화력을 다음과 같은 분석방법으로 얻었다:
얼음 상에서 필요로 하는 멤브레인 단백질 0.075㎍/㎕, 사포닌 10㎕/㎖, GDP 3μM 및 [35S]GTPγS 0.20nM의 최종 농축물을 결합 완충액(100mM NaCl, 10mM MgCl2, 20mM HEPES, pH 7.4)에 순차적으로 첨가하여 뮤(μ) 오피오이드 수용체 멤브레인 수용액을 제조하였다. 제조된 멤브레인 용액(190㎕/웰)을 DMSO 중에서 제조된 효능제의 20배의 농축 저장 용액 10㎕를 함유하는 96-shallow well 폴리프로필렌 플레이트에 전사하였다. 플레이트를 진동시키면서 실온에서 30분 동안 배양하였다. 반응물을 96-웰 조직 수확기(Brandel)를 이용하여 96-웰 Unifilter GF/B 필터 플레이트(Packard) 상으로 고속 여과하여 측정하고 얼음 냉각된 결합 완충액(10mM NaH2PO4, 10mM Na2HPO4, pH7.4) 200㎕로 세 번 여과 세척하였다. 필터 플레이트를 이어서 2 내지 3시간 동안 50℃에서 건조하였다. 50 ㎕/웰 신틸레이션 칵테일(scintillation cocktail)(MicroScint20, Packard)을 첨가하고 플레이트를 Packard Top-Counts 내에서 1min/웰 동안 세었다.
데이터를 GraphPad PRISMMTM, v.3.0으로써 곡선형 함수를 이용하여 분석하여 그 결과를 다음 표 2에 나타내었다.
[표 2]
본 발명의 화합물은 진통제, 항-염증제(anti-inflammatory), 이뇨제(diuretic), 마취제(anesthetic), 및 신경보호제(neuroprotective agents), 항-고혈압(anti-hypertensive), 항-불안완화제(anti-anxioltics); 식욕 억제제(agent for appetite control); 청력 조절제(hearing regulators); 항-기침성(anti-tussive), 항-천식성(anti-asthmatics), 이동 활성의 조절(modulators of locomotor activity), 학습 및 기억력의 조절(modulators of learning and memory), 신경전달물질 및 호르몬 방출의 조절, 신장 기능 조절, 항-진정제(anti-depressant), 알츠하이머병 또는 다른 치매로 인한 기억력 손실을 치료하는 약물, 항-간질병(anti-epileptics), 항-경련제(anti-convulsant), 알콜 및 약물 중독으로부터 금단 증상을 치료하기 위한 약물, 수분 밸런스 조절 약물, 소듐 배출 치료용 약물 및 동맥의 혈압 이상을 조절하기 위한 약물과 같은 곳에 유용하게 사용될 뿐만 아니라, 이러한 화합물을 투여하기 위한 방법을 제공하는 데도 유용하다.
Claims (31)
- 화학식 1의 화합물:화학식 1상기 식에서,W는 수소원자, C1-10의 알킬, C3-12의 사이클로알킬, C3-12의 사이클로알킬C1-4알킬-, C1-10의 알콕시, C3-12의 사이클로알콕시-, 1 내지 3의 할로겐으로 치환된 C1-10의 알킬, 1 내지 3의 할로겐으로 치환된 C3-12의 사이클로알킬, 1 내지 3의 할로겐으로 치환된 C3-12사이클로알킬C1-4알킬-, 1 내지 3의 할로겐으로 치환된 C1-10의 알콕시, 1 내지 3의 할로겐으로 치환된 C3-12의 사이클로알콕시-, -COOV1, -C1-4COOV1, -CH2OH, -SO2N(V1)2, 하이드록시C1-10알킬-, 하이드록시C3-10사이클로알킬-, 시아노C1-10알킬-, 시아노C3-10사이클로알킬-, CON(V1)2, NH2SO2C1-4알킬-, NH2SOC1-4알킬-, 술포닐아미노C1-10알킬-, 디아미노알킬-, -술포닐C1-4알킬, 6-원 헤테로사이클릭환, 6-원 헤테로방향족환, 6-원 헤테로사이클릭C1-4알킬-, 6-원 헤테로방향족 C1-4알킬-, 6-원 방향족환, 6-원 방향족C1-4알킬-, 옥소 또는 티오로써 임의적으로 치환된 5-원 헤테로사이클릭환, 5-원 헤테로방향족환, 옥소 또는 티오로써 임의적으로 치환된 5-원 헤테로사이클릭C1-4알킬-, 5원 헤테로방향족C1-4알킬-, -C1-5(=O)W1, -C1-5(=NH)W1, -C1-5NHC(=O)W1, -C1-5NHS(=O)2W1, -C1-5NHS(=O)W1, 여기서 W1은 수소원자, C1-10의 알킬, C3-12의 사이클로알킬, C1-10의 알콕시, C3-12의 사이클로알콕시, -CH2OH, 아미노, C1-4의 알킬아미노-, 디C1-4알킬아미노-, 또는 1 내지 3의 저급 알킬로써 임의적으로 치환된 5-원 헤테로방향족환이며;상기 식에서 각각의 V1은 H, C1-6의 알킬, C3-6의 사이클로알킬, 벤질 또는 페닐로부터 독립적으로 선택된 것이고;Q는 C1-8알킬, 5 내지 8-원 사이클로알킬, 5 내지 8-원 헤테로사이클릭 또는 6원 방향족 또는 헤테로방향족기이며;n은 독립적으로 0 내지 3의 정수이며;A, B 및 C는 독립적으로 수소원자, C1-10의 알킬, C3-12의 사이클로알킬, C1-10의 알콕시, C3-12의 사이클로알콕시, -CH2OH, -NHSO2, 하이드록시C1-10알킬-, 아미노카보닐-, C1-4알킬아미노카보닐-, 디C1-4알킬아미노카보닐-, 아실아미노-, 아실아미노알킬-, 아미드, 술포닐아미노C1-10알킬-, 또는 A-B는 함께 C2-6브릿지를 형성할 수 있거나, 또는 B-C는 함께 C3-7브릿지를 형성할 수 있거나, 또는 A-C는 함께 C1-5브릿지를 형성할 수 있으며;Z는 결합사슬, 직쇄상 또는 가지상 C1-6알킬렌, -NH-, -CH2O-, -CH2NH-, -CH2N(CH3)-, -NHCH2-, -CH2CONH-, -NHCH2CO-, -CH2CO-, -COCH2-, -CH2COCH2-, -CH(CH3)-, -CH=, -0- 및 -HC=CH-으로 이루어진 군으로부터 선택된 것이며, 여기서 탄소 및/또는 질소 원자들은 하나 또는 그 이상의 저급 알킬, 하이드록시, 할로 또는 알콕시기로써 치환되거나 치환되지 않은 것들이며;R1은 수소원자, C1-10의 알킬, C3-12의 사이클로알킬, C2-10의 알케닐, 아미노, C1-10의 알킬아미노-, C3-12의 사이클로알킬아미노-, -COOV1, -C1-4COOV1, 시아노, 시아노C1-10알킬-, 시아노C3-10사이클로알킬-, NH2SO2-, NH2SO2C1-4알킬-, NH2SOC1-4알킬-, 아미노카보닐-, C1-4의 알킬아미노카보닐-, 디C1-4알킬아미노카보닐-, 벤질, C3-12의 사이클로알케닐-, 모노사이클릭, 바이사이클릭 또는 트리사이클릭 아릴 또는 헤테로아릴환, 헤테로-모노사이클릭 환, 헤테로-바이사이클릭환 시스템 및 다음 화학식 2의 스피로환 시스템:화학식 2상기 식에서, X1및 X2는 독립적으로 NH, O, S 및 CH2로부터 선택된 것이고; 그리고 상기 R1의 알킬, 사이클로알킬, 알케닐, C1-10알킬아미노-, C3-12사이클로알킬아미노-, 또는 벤질은 할로겐, 하이드록시, C1-10알킬, C1-10알콕시, 니트로, 트리플루오로메틸-, 시아노, -COOV1, -C1-4COOV1, 시아노C1-10알킬-, -C1-5(=O)W1, -C1-5NHS(=O)2W1, -C1-5NHS(=O)W1, 5-원 헤테로방향족C0-4알킬-, 페닐, 벤질, 벤질옥시(여기서, 페닐, 벤질 및 벤질옥시는 할로겐, C1-10알킬-, C1-10알콕시- 및 시아노로 이루어진 군으로부터 선택된 1 내지 3의 치환체들로써 임의적으로 치환된 것이다)로 이루어진 군으로부터 선택된 1 내지 3의 치환체들로써 임의적으로 치환된 것이고; 그리고 상기 C3-12의 사이클로알킬, C3-12의 사이클로알케닐, 모노사이클릭, 바이사이클릭 또는 트리사이클릭 아릴, 헤테로아릴환, 헤테로-모노사이클릭환, 헤테로-바이사이클릭환 시스템, 또는 화학식 ii의 스피로환 시스템은 할로겐, C1-10알킬, C1-10알콕시, 니트로, 트리플루오로메틸-, 페닐, 벤질, 페닐옥시 및 벤질옥시(여기서, 페닐, 벤질, 페닐옥시 또는 벤질옥시는 할로겐, C1-10알킬, C1-10알콕시 및 시아노로 이루어진 군으로부터 선택된 1 내지 3의 치환체들로써 임의적으로 치환되어진 것이다)로이루어진 군으로부터 선택된 1 내지 3의 치환체들로써 임의적으로 치환된 것이며;R2는 수소원자, C1-10알킬, C3-12사이클로알킬 및 할로겐으로 이루어진 군으로부터 선택된 것으로서, 여기서 알킬 또는 사이클로알킬은 옥소, 아미노, 알킬아미노 또는 디알킬아미노기로써 임의적으로 치환된 것이고;또는 약학적으로 용인된 이들의 염 또는 이들의 용매화물(solvate).
- 제 1 항에 있어서, Q는 페닐 또는 1 내지 3의 질소원자를 함유하는 6-원 헤테로방향족기인 것임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 상기 W는 -CH2C=ONH2, -C(NH)NH2, 피리딜메틸, 사이클로펜틸, 사이클로헥실, 퓨라닐메틸, -C=OCH3, -CH2CH2NHC=OCH3, -SO2CH3, CH2CH2NHSO2CH3, 퓨라닐카보닐-, 메틸피롤릴카보닐-, 디아졸카보닐-, 아졸메틸-, 트리플루오로에틸-, 하이드록시에틸-, 시아노메틸-, 옥소-옥사졸메틸- 및 디아졸메틸- 로 이루어진 군으로부터 선택된 것임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 상기 ZR1은 사이클로헥실에틸-, 사이클로헥실메틸-, 사이클로펜틸메틸-, 디메틸사이클로헥실메틸-, 페닐에틸-, 피롤릴트리플루오로에틸-, 트리에닐트리플루오로에틸-, 피리딜에틸-, 사이클로펜틸-, 사이클로헥실-, 메톡시사이클로헥실-, 테트라하이드로피라닐-, 프로필피페리디닐-, 인돌릴메틸-, 피라졸릴펜틸-, 티아졸릴에틸-, 페닐트리플루오로에틸-, 하이드록시헥실-, 메톡시헥실-, 이소프로폭시부틸-, 헥실- 및 옥소카닐프로필- 로 이루어진 군으로부터 선택된 것임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 상기 ZR1또는 W 중의 적어도 하나는 -CH2COOV1, 테트라졸릴메틸-, 시아노메틸-, NH2SO2메틸-, NH2SO메틸-, 아미노카보닐메틸-, C1-4알킬아미노카보닐메틸- 및 디C1-4알킬아미노카보닐메틸- 로 이루어진 군으로부터 선택된 것임을 특징으로 하는 화합물.
- 제 1 항에 있어서, 상기 ZR1은 -COOV1, 테트라졸릴 C0-4알킬-, 시아노-, 아미노카보닐-, C1-4알킬아미노카보닐-, 또는 디 C1-4알킨아미노카보닐- 로써 프로필의 3탄소에 임의적으로 치환된 3,3 디페닐프로필인 것임을 특징으로 하는 화합물.
- 다음 화학식 3의 화합물:화학식 3상기 식에서, n은 0 내지 3의 정수이고;Z는 결합사슬, -CH2-, -NH-, -CH2O-, -CH2CH2-, -CH2NH-, -CH2N(CH3), -NHCH2-, -CH2CONH-, -NHCH2CO-, -CH2CO-, -COCH2-, -CH2COCH2-, -CH(CH3)-, -CH= 및 -HC=CH-으로 이루어진 군으로부터 선택된 것이며, 여기서 탄소 및/또는 질소 원자들은 저급알킬, 할로겐, 하이드록시 또는 알콕시기로써 치환되거나 치환되지 않은 것들이며;R1은 수소원자, C1-10의 알킬, C3-12의 사이클로알킬, C2-10의 알케닐, 아미노, C1-10의 알킬아미노, C3-12의 사이클로알킬아미노, 벤질, C3-12의 사이클로알케닐, 모노사이클릭, 바이사이클릭 또는 트리사이클릭 아릴 또는 헤테로아릴환, 헤테로-모노사이클릭 환, 헤테로-바이사이클릭환 시스템 및 다음 화학식 2의 스피로환 시스템:화학식 2상기 식에서, X1및 X2는 독립적으로 NH, O, S 및 CH2로부터 선택된 것이고;여기서 알킬, 사이클로알킬, 알케닐, C1-10알킬아미노, C3-12사이클로알킬아미노, 또는 벤질은 할로겐, C1-10알킬, C1-10알콕시, 니트로, 트리플루오로메틸, 시아노, 페닐, 벤질, 벤질옥시(여기서, 페닐, 벤질 및 벤질옥시는 할로겐, C1-10알킬, C1-10알콕시 및 시아노로 이루어진 군으로부터 선택된 1 내지 3의 치환체들로써 임의적으로 치환되어진 것이다)로 이루어진 군으로부터 선택된 1 내지 3의 치환체들로써 임의적으로 치환된 것이고;상기 C3-12의 사이클로알킬, C3-12의사이클로알케닐, 모노사이클릭, 바이사이클릭 또는 트리사이클릭 아릴, 헤테로아릴환, 헤테로-모노사이클릭환, 헤테로-바이사이클릭환 시스템, 및 상기 화학식 2의 스피로환 시스템은 할로겐, C1-10알킬, C1-10알콕시, 니트로, 트리플루오로메틸, 페닐, 벤질, 페닐옥시 및 벤질옥시(여기서, 페닐, 벤질, 페닐옥시 및 벤질옥시는 할로겐, C1-10알킬, C1-10알콕시 및 시아노로 이루어진 군으로부터 선택된 1 내지 3의 치환체들로써 임의적으로 치환되어진 것이다)로 이루어진 군으로부터 선택된 1 내지 3의 치환체들로써 임의적으로 치환된 것이며;R2는 수소원자, C1-10알킬, C3-12사이클로알킬 및 할로겐으로 이루어진 군으로부터 선택된 것으로서, 여기서 알킬은 옥소기로써 임의적으로 치환된 것이며;또는 약학적으로 용인된 이들의 염.
- 제 7 항에 있어서, R1은 메틸, 에틸, 프로필, 부틸, 펜틸, 및 헥실로 이루어진 군으로부터 선택된 알킬인 것임을 특징으로 하는 화합물.
- 제 7 항에 있어서, 상기 R1은 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 사이클로노닐, 사이클로데실 및 노보닐로 이루어진 군으로부터 선택된 사이클로알킬인 것임을 특징으로 하는 화합물.
- 제 7 항에 있어서, 상기 R1은 테트라하이드로나프틸, 데카하이드로나프틸 또는 디벤조사이클로헵틸인 것임을 특징으로 하는 화합물.
- 제 7 항에 있어서, R1은 페닐 또는 벤질인 것임을 특징으로 하는 화합물.
- 제 7 항에 있어서, R1은 바이사이클릭 방향족환인 것임을 특징으로 하는 화합물.
- 제 12 항에 있어서, 상기 바이사이클릭 방향족환은 인데닐, 퀴놀린 또는 나프틸인 것임을 특징으로 하는 화합물.
- 제 7 항에 있어서, 상기 Z는 결합사슬, 메틸 또는 에틸인 것임을 특징으로 하는 화합물.
- 제 7 항에 있어서, 상기 n은 0인 것임을 특징으로 하는 화합물.
- 제 7 항에 있어서, 상기 X1및 X2는 모두 0인 것임을 특징으로 하는 화합물.
- 다음 군으로부터 선택된 화합물:8-(4-프로필사이클로헥실)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(5-메틸헥스-2-일)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-노보닐-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(데카하이드로-2-나프틸)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(사이클로옥틸메틸)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(1,2,3,4-테트라하이드로-2-나프틸)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-[4-(2-프로필)-사이클로헥실)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(1,3-디하이드로인덴-2-일)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-[(나프트-2-일-메틸)]-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(p-페닐벤질)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-[4,4-비스(4-플루오로페닐)부틸]-1-페닐-2,3,8-트리아조스피로[4.5]대칸-4-온;8-(벤질)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(10,11-디하이드로-5H-디벤조[a.d]-사이클로헵텐-5-일)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(3,3-비스(페닐)프로필)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(p-벤질옥시벤질)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;8-(사이클로옥틸메틸)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온;및약학적으로 용인된 이들의 염.
- 8-(아세나프텐-9-일)-1-페닐-2,3,8-트리아조스피로[4.5]데칸-4-온 또는 약학적으로 용인된 이들의 염 또는 이들의 용매화물인 화합물.
- 제 1 항의 화합물과 적어도 하나의 약학적으로 용인된 부형제를 포함하는 약학 조성물.
- 제 1 항에 따른 진통제 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 통증 처치방법.
- 제 1 항에 따른 진통제 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 ORL1 수용체로부터 약력학 감응을 조정하는 방법.
- 제 7 항의 화합물과 적어도 하나의 약학적으로 용인된 부형제를 포함하는 약학 조성물.
- 제 7 항에 따른 진통제 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 통증 처치방법.
- 제 7 항에 따른 진통제 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 ORL1 수용체로부터 약력학 감응을 조정하는 방법.
- 다음 화학식 3으로 표시되는 화합물:화학식 3상기 식에서, R2는 수소원자, C1-10알킬, C3-12의 사이클로알킬 및 할로겐으로 이루어진 군으로부터 선택된 것으로, 상기 알킬은 옥소기로써 임의적으로 치환된 것이며;n은 0 내지 3의 정수이고;그리고 ZR1은이며, 여기서 Y1은 R3-(C1-C12)알킬, R4-아릴, R5-헤테로아릴, R6-(C3-C12)사이클로-알킬, R7-(C3-C7)헤테로사이클로알킬, -CO2(C1-C6)알킬, CN 또는 -C(O)NR8R9이고; Y2는 수소원자 또는 Y1이고; Y3는 수소원자 또는 (C1-C6)알킬이며; 또는 Y1, Y2및 Y3는 다음 구조 중의 하나의 형태로 탄소원자와 함께 결합되어질 수 있으며:상기 식에서 r은 0 내지 3이고; w와 u는 각각 0 내지 3으로, w와 u의 합은 1-3을 만족하며; c와 d는 독립적으로 1 또는 2이고; s는 1 내지 5이며; 그리고 고리 E는 퓨즈드 R4-페닐 또는 R5-헤테로아릴환이며;R10은 H, (C1-C6)알킬, -OR8, -(C1-C6)알킬-OR8, -NR8R9및 -(C1-C6)알킬-NR8R9으로 이루어진 군으로부터 선택된 독립적인 1 내지 3의 치환체들이며;R11은 R10, -CF3, -OCF3, NO2및 할로로 이루어진 군으로부터 독립적으로 선택된 1 내지 3의 치환체들이고, 또는 인접한 고리의 탄소원자 상에 R11치환체는 메틸렌디옥시 또는 에틸렌디옥시환을 함께 형성할 수 있으며;R8과 R9은 독립적으로 수소원자, (C1-C6)알킬, (C3-C12)사이클로알킬, 아릴 및아릴(C1-C6)알킬로 이루어진 군으로부터 선택된 것이고;R3는 H, R4-아릴, R6-(C3-C12)사이클로알킬, R5-헤테로아릴, R7-(C3-C7)헤테로사이클로알킬, -NR8R9, -OR12및 -S(0)0-2R12로 이루어진 군으로부터 독립적으로 선택된 1 내지 3의 치환체이며;R6는 H, (C1-C6)알킬, R4-아릴, -NR8R9, -OR12및 -SR12로 이루어진 군으로부터 독립적으로 선택된 1 내지 3의 치환체이며;R4는 수소원자, 할로, (C1-C6)알킬, R13-아릴, (C3-C12)사이클로알킬, -CN, -CF3, -OR8, -(C1-C6)알킬-OR8, -OCF3, -NR8R9, -(C1-C6)알킬-NR8R9, -NHSO2R8, -SO2N(R14)2, -SO2R8, -SOR8, -SR8, -NO2, -CONR8R9, -NR9COR8, -COR8, -COCF3, -OCOR8, -OCO2R8, -COOR8, -(C1-C6)알킬-NHCOOC(CH3)3, -(C1-C6)알킬-NHCOCF3, -(C1-C6)알킬-NHSO2-(C1-C6)알킬, -(C1-C6)알킬-NHCONH-(C1-C6)-알킬 및(여기서, f는 0 내지 6이고; 또는 인접한 고리 탄소원자 상에 R4치환체는 함께 메틸렌디옥시 또는 에틸렌디옥시환을 형성할 수 있다)으로 이루어진 군으로부터 독립적으로 선택된 1 내지 3 치환체이고;R5는 수소원자, 할로, (C1-C6)알킬, R13-아릴, (C3-C12)사이클로알킬, -CN, -CF3, -OR8, -(C1-C6)알킬-OR8, -OCF3, -NR8R9, -(C1-C6)알킬-NR8R9, -NHSO2R8, -SO2N(R14)2, -NO2, -CONR8R9, -NR9COR8, -COR8, -OCOR8, -OCO2R8및 -COOR8로 이루어진 군으로부터 독립적으로 선택된 1 내지 3의 치환체이고;R7은 H, (C1-C6)알킬, -OR8, -(C1-C6)알킬-OR8, -NR8R9또는 -(C1-C6)알킬-NR8R9;R12는 H, (C1-C6)알킬, R4-아릴, -(C1-C6)알킬-OR8, -(C1-C6)알킬-NR8R9, -(C1-C6)알킬-SR8, 또는 아릴(C1-C6)알킬이고;R13은 H, (C1-C6)알킬, (C1-C6)알콕시 및 할로로 이루어진 군으로부터 독립적으로 선택된 1 내지 3의 치환체이며;R14는 H, (C1-C6)알킬 및 R13-C6H4-CH2-로 이루어진 군으로부터 독립적으로 선택된 것이며;또는 이들의 약학적으로 용인된 염.
- 제 25 항의 화합물과 적어도 하나의 약학적으로 용인된 부형제를 포함하는 약학 조성물.
- 제 25 항에 따른 진통제 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 통증처치 방법.
- 제 25 항에 따른 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 ORL1 수용체로부터 약력학 감응을 조정하는 방법.
- 제 1 항에 따른 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 오피오이드 수용체로부터 약력학 감응을 조정하는 방법.
- 제 7 항에 따른 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 오피오이드 수용체로부터 약력학 감응을 조정하는 방법.
- 제 25 항에 따른 화합물의 유효량을 이를 필요로 하는 환자에게 투여하는 것을 포함하는 오피오이드 수용체로부터 약력학 감응을 조정하는 방법.
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