KR920002588A - 신규 3-아릴인돌 및 3-아릴인다졸 유도체 - Google Patents
신규 3-아릴인돌 및 3-아릴인다졸 유도체 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 238000000034 method Methods 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical group S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- -1 imidazolidin-2-one- 1-yl Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 238000007142 ring opening reaction Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JHXVZNYMJMMPEI-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,5-dimethyl-1-(1-methylpiperidin-4-yl)indole Chemical compound C1CN(C)CCC1N1C2=CC=C(C)C=C2C(C=2C=CC(F)=CC=2)=C1C JHXVZNYMJMMPEI-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical class ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical class CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical group ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- 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
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
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- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 식 I :의 3-아릴인돌 또는 3-아릴인다졸 유도체와 이것의 약학적 허용 산부가염 및 프로드럭.상기식에서, Ar은 할로겐, 저급알킬, 저급알콕시, 히드록시, 트리플루오로 메틸 및 시아노로부터 선택되는 하나 또는 그 이상의 치환기로 선택적으로 치환된 페닐이거나 또는 Ar은 2-티에닐, 3-티에닐, 2-푸릴, 3-푸릴, 2-피리딜, 3-피리딜 또는 4-피리딜이고; R1내지 R4는 수소, 할로겐, 저급알킬, 저급알콕시, 히드록시, 니트로, 저급알킬티오, 저급알킬술포닐, 저급알킬아미노, 저급디알킬아미노, 시아노, 트리플루오로메틸 또는 트리플루오로메틸티오로부터 독립적으로 선택되고; 고리시스템의 X로부터 나온 점선은 선택적 결합을 의미하고, 상기 점선이 결합을 의미할때는 X는 질소 또는 CR6기(R6은 수소, 할로겐, 트리플루오로메틸 또는 저급알킬이다)이고, 상기 점선이 결합을 의미하지 않을때는 X는 CH2이고; Y로 부터 나온 점선은 선택적 결합을 의미하고, 이 점선이 결합을 의미할때에는 Y는 N 또는 CH이고, 결합을 의미할 때에는 Y는 C이고; R5는 수소, 또는 하나 또는 둘의 히드록시기로 선택적으로 치환된 시클로알킬, 시클로알킬알킬, 저급알킬 또는 저급알케닐이거나 또는 R5는 구조식 1a 및 1b :[상기에서, n은 2 내지 6의 정수이고, W는 산소 또는 황이고, U는 질소 또는 CH이고, Z는 -(CH2)m-(m은 2 또는 3)이거나 또는 Z는 할로겐 또는 트리플루오로메틸로 선택적으로 치환된 1,2-페닐렌이거나 또는 Z는 -CH=CH-, -COCH2- 또는 -CSCH2-이고, V는 산소, 황, CH2또는 NR7(R7은 수소, 또는 하나 또는 둘의 히드록시기로 선택적으로 치환된 저급알킬, 저급알케닐, 시클로알킬 또는 시클로알킬알킬이다)이고, U1은 산소, 황, CH2또는 NR8기(R8은 수소, 또는 하나 또는 둘의 히드록시기로 선택적으로 치환된 저급알킬, 저급알케닐, 시클로알킬 또는 시클로알킬알킬이다)이고, 그리고 V1은 NR9R10,OR11,SR12또는 CR13R14R15(R9내지 R15의 각각은 R8-치환기 중에서 독립적으로 선택될 수 있다)이다]로부터 선택된 기이고, 단 R5는 R1내지 R4의 각각이 수소이고 X와 Y가 CH이고 Ar이 페닐일 경우 메틸이 아닐 수 있다.
- 제1항에 있어서, Ar이 할로겐으로 선택적으로 치환된 페닐 바람직하게는 4-플루오로페닐인 것을 특징으로하는 유도체.
- 제1항 또는 제2항의 어느 한 항에 있어서, R5가 식:의 기인것을 특징으로 하는 유도체.상기식에서, R7,R8,R9및 R10은 수소, 저급알킬 및 저급알케닐로 부터 독립적으로 선택된다.
- 제1항 내지 제3항중의 어느 한 항에 있어서, X가 CR6인 것을 특징으로 하는 유도체.
- 제4항에 있어서, R2및/또는 R6가 수소가 아닌 것을 특징으로 하는 유도체.
- 제1항 내지 제5항중의 어느 한 항에 있어서, R2는 할로겐, -CH3및 -CF3로부터 선택되고 및/또는 R3는 수소, 할로겐, -CH3및 -CF3로부터 선택되는 것을 특징으로 하는 유도체.
- 제1항에 있어서, 5-클로로-3-(4-플루오로페닐)-1-[1-[2-(3-메틸이미다졸리딘-3-온-1-일)에닐]-4-피페리딜]-1H-인돌, 3-(4-플루오로페닐)-1-[1-[2-(이미아졸리딘-2-온-1-일)에닐]-4-피페리딜]-5-메틸-1H-인돌, 3-(4-플루오로페닐)-5-메틸-1-[1-[2-[3-(2-프로필)이미다졸린딘-2-온-1-일]에닐]-4-피페리딜]-1H-인돌, 2,5-디메틸-3-(4-플루오로페닐)-1-[1-(2-(이미다졸리딘-2-온-1-일)에틸]-1,2,3,6-테트라히드로피리딘-4-일]-1H-인돌, 2,5-디메틸-3-(4-플루오로페닐)-1-[1-[2-(이미다졸리딘-2-온-1-일)에닐]-4-피페리딜]-1H-인돌, 2,5-디메틸-3-(4-플루오로페닐)-1-(1-메틸-4-피페리딜)-1H-인돌, 또는 1-[1-[2-(1,3-디메틸-1-우레이도)에틸]-4-피페리딜]-3-(4-플루오로페닐)-5-메틸-1H-인돌인 것을 특징으로하는 유도체.
- 약학적 허용 담체 또는 희석재와 함께 제1항 내지 제7항중의 어느 한항의 화합물 또는 그것의 약학적 허용염 또는 프로드럭으로 이루어지는 것을 특징으로하는 약학적 조성물.
- 불안, 난폭, 정신분열병의 음성적 증상, 우울, 편두통, 수면장애, 약물-유발 파킨슨 증후군 또는 파킨슨 질환의 치료용 약제를 제조하기 위한 제1항 내지 제7항중의 어느 한 항의 유도체 또는 그것의 약학적 허용염 또는 프로드럭의 사용.
- a) 식 :의 화합물(R1,R2,R3,R4,X,Y,Ar 및 점선은 상기에서 정의한 바와 같다)을 저급 알킬 할라이드, 알킬 메실레이트 또는 토실레이트 또는 식 :(R'은 수소, 메틸 또는 에틸이다)의 에폭시드 또는 식 :의 할라이드(n,W,U,V,Z,V1및 U1은 상기에서 정의한 바와 같다)와 반응시키는 방법, 또는 b) 식:의 화합물(R1,R2,R3,R4,R6,Ar 및 점선은 상기에서 정의한 바와 같다)을 식:R5N(CH2CH2hal)2(Ⅴ)의 화합물(R5는 상기에서 정의한 바와 같고 hal은 할로겐이다)과 반응시키는 방법, 또는 c) 식:의 화합물(R1내지 R5,Ar,Y 및 점선은 상기에서 정의한 바와 같다)의 인돌고리를 디히드로인돌고리로 환원시키는 방법, 또는 d) 식:의 화합물 (R1내지 R5,X,Ar,및 점선은 상기에서 정의된 바와 같다)에서 테트라히드로피리딜 고리의 이중결합을 환원시키는 방법, 또는 e) 식:의 화합물 (R1내지 R5,X,Ar,및 점선은 상기에서 정의된 바와 같다. 단 R5는 수소는 아니다. hal은 할로겐이다)의 피리디늄 고리를 테트라 히드로피리딘 고리로 환원시키는 방법, 또는 f) 상기식 Ⅷ 화합물의 피리디늄고리 도는 식 XⅣ의 화합물의 피리딜고리를 피페라딘 고리로 환원시키는 방법, 또는 g) 식:의 화합물(R1내지 R4,X,Y,Ar 및 점선은 상기에서 정의된 바와 같고 R16은 수소, 저급알킬 또는 저급알콕시이다)카르보닐기를 환원시키는 방법, 또는 h) 식:의 아미노알킬유도체(R1내지 R4,X,Y,Ar,R8,n 및 점선은 상기에서 정의된 바와 같다)을 할로겐화 카르복실산, 안하이드라드 또는 혼합 안하이드라이드, 또는 카르바밀 클로라이드, 티오카르바밀 클로라이드, 이소시아네이트, 이소티오시아네이트 또는 치환 클로로포르메이트 등과 같은 아실화 시약으로 아실화시키는 방법, 또는 i) 식:의 중간생성물 에틸렌 또는 프로필렌 디아민 유도체(R1내지 R4,R8,n,X,Y,Ar 및 점선은 상기에서 정의된 바와 같고 m은 2 또는 3이다)을 포스켄, 티오포스겐 또는 카본디설파이드로 고리개환반응시켜 구조식 la의 치환기를 생성하는 방법, 또는 j) 식:의 카르복실산 또는 카르복실산 유도체(R1내지 R4,X,Y,Ar 및 점선은 상기에서 정의된 바와 같고 R17은 수소 또는 저급알킬이고 p는 1,2 또는 3이다)을 개환반응시키는 방법으로 이루어지고, 그리고 바람직하다면 (a) 내지 (j) 방법중의 한 방법에 의해 제조된 식 I (R5는 V가 NH이고 또는 V1이 NHR19이고 또는 U1이 NH인 구조식 1a 또는 1b이다)의 화합물을 아실화시약으로 아실화시키거나 또는 식 I 화합물의 이용가능한 히드록시기를 에스테르화시켜 프로드럭을 얻고, 또는 (a) 내지 (j) 방법중의 한 방법에 의하여 제조된 화합물을 그것의 약학적 허용 산부가염으로 전환시키고, 또는 (a) 내지 (j) 방법중의 한 방법에 의하여 제조된 식 I의 광학적 활성 화합물을 그것의 광학적 활성 이성질체로 분해하는 것으로 이루어지는, 제1항 유도체의 제조방법.※참고사항:최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK181190A DK181190D0 (da) | 1990-07-30 | 1990-07-30 | 3-aryl-indol- eller 3-aryl-indazolderivater |
| DK1811/90 | 1990-07-30 | ||
| SG19995A SG19995G (en) | 1990-07-30 | 1995-02-07 | Novel 3-arylindole and 3-arylindazole derivatives |
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| Publication Number | Publication Date |
|---|---|
| KR920002588A true KR920002588A (ko) | 1992-02-28 |
| KR100233955B1 KR100233955B1 (ko) | 2000-02-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910012971A KR100233955B1 (ko) | 1990-07-30 | 1991-07-27 | 신규 3-아릴인돌 및 3-아릴인다졸 유도체 |
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| Country | Link |
|---|---|
| US (1) | US5393761A (ko) |
| EP (1) | EP0470039B1 (ko) |
| JP (1) | JP3165181B2 (ko) |
| KR (1) | KR100233955B1 (ko) |
| AT (1) | ATE115128T1 (ko) |
| AU (1) | AU646679B2 (ko) |
| CA (1) | CA2048027C (ko) |
| DE (1) | DE69105659T2 (ko) |
| DK (2) | DK181190D0 (ko) |
| ES (1) | ES2064974T3 (ko) |
| FI (1) | FI99111C (ko) |
| GR (1) | GR3015274T3 (ko) |
| HK (1) | HK51495A (ko) |
| IE (1) | IE65673B1 (ko) |
| IL (1) | IL98829A (ko) |
| NO (1) | NO178192C (ko) |
| NZ (1) | NZ238956A (ko) |
| PT (1) | PT98483B (ko) |
| SG (1) | SG19995G (ko) |
| ZA (1) | ZA915805B (ko) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5643784A (en) * | 1990-12-04 | 1997-07-01 | H, Lundbeck A/S | Indan derivatives |
| NZ243065A (en) | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| DK8492D0 (da) * | 1992-01-23 | 1992-01-23 | Lundbeck & Co As H | Behandling af psykoser |
| US5264576A (en) * | 1992-10-22 | 1993-11-23 | Hoechst-Roussel Pharmaceuticals Incorporated | Pyrazolo[4,3-c]pyridines which are intermediates |
| TW421649B (en) * | 1995-01-31 | 2001-02-11 | Janssen Pharmaceutica Nv | 4-(1H-indol-1yl)-1-piperidinyl derivatives |
| GB9523462D0 (en) * | 1995-11-16 | 1996-01-17 | Merck Sharp & Dohme | Therapeutic agents |
| FR2744452B1 (fr) * | 1996-02-06 | 1998-03-06 | Cird Galderma | Composes biaryles heterocycliques, compositions pharmaceutiques et cosmetiques les contenant et utilisations |
| DE19642255A1 (de) * | 1996-10-14 | 1998-04-16 | Bayer Ag | Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten |
| TWI242011B (en) | 1997-03-31 | 2005-10-21 | Eisai Co Ltd | 1,4-substituted cyclic amine derivatives |
| FR2788772B1 (fr) * | 1999-01-26 | 2001-03-02 | Adir | Nouveaux composes cyano-indoles inhibiteurs de recapture de serotonine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AU2001274049A1 (en) | 2000-05-26 | 2001-12-11 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of indole derivatives and intermediates of the process |
| DK1392676T3 (da) * | 2001-02-16 | 2007-04-10 | Aventis Pharma Inc | Hidtil ukendte heterocykliske urinstofderivater og deres anvendelse som dopamin -D3 - receptorligander |
| GB0117950D0 (en) * | 2001-02-16 | 2001-09-19 | Aventis Pharma Inc | Novel heterocyclic urea derivatives andd their use as dopamine D3 receptor ligands |
| US6951871B2 (en) | 2002-06-24 | 2005-10-04 | Schering Corporation | Indole derivatives useful as histamine H3 antagonists |
| TW200409759A (en) | 2002-09-25 | 2004-06-16 | Wyeth Corp | Substituted 4-(indazol-3-yl)phenols |
| GB0306604D0 (en) * | 2003-03-21 | 2003-04-30 | Curidium Ltd | Second medical use |
| US20060004043A1 (en) | 2003-11-19 | 2006-01-05 | Bhagwat Shripad S | Indazole compounds and methods of use thereof |
| DE102006043443A1 (de) * | 2006-09-15 | 2008-03-27 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| US9963458B2 (en) | 2012-12-27 | 2018-05-08 | Purdue Pharma L.P. | Indole and indoline-type piperidine compounds and uses thereof |
| EP2958914B1 (en) | 2013-02-21 | 2020-07-15 | Adverio Pharma GmbH | Forms of methyl {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridino-3-yl]pyrimidino-5-yl}methyl carbamate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2354766A1 (fr) * | 1976-06-17 | 1978-01-13 | Labaz | Derives n-aminoalkyles d'indole et procedes pour les preparer |
| FR2421900A1 (fr) * | 1977-03-17 | 1979-11-02 | Sauba Lab | Piperazino-3-indoles, leur procede de preparation et leurs applications therapeutiques |
| HU198036B (en) * | 1983-08-22 | 1989-07-28 | Hoechst Roussel Pharma | Process for production of derivatives of 3-piperidil-/1h/-indasole and medical preparatives containing them |
| DK704488D0 (da) * | 1988-12-19 | 1988-12-19 | Novo Industri As | Nye n-substituerede azaheterocykliske carboxylsyrer |
| IE58370B1 (en) * | 1985-04-10 | 1993-09-08 | Lundbeck & Co As H | Indole derivatives |
-
1990
- 1990-07-30 DK DK181190A patent/DK181190D0/da not_active Application Discontinuation
-
1991
- 1991-07-09 IE IE240391A patent/IE65673B1/en not_active IP Right Cessation
- 1991-07-12 NZ NZ238956A patent/NZ238956A/xx unknown
- 1991-07-12 NO NO912739A patent/NO178192C/no not_active IP Right Cessation
- 1991-07-15 IL IL98829A patent/IL98829A/en not_active IP Right Cessation
- 1991-07-22 EP EP91610058A patent/EP0470039B1/en not_active Expired - Lifetime
- 1991-07-22 ES ES91610058T patent/ES2064974T3/es not_active Expired - Lifetime
- 1991-07-22 DE DE69105659T patent/DE69105659T2/de not_active Expired - Fee Related
- 1991-07-22 AT AT91610058T patent/ATE115128T1/de not_active IP Right Cessation
- 1991-07-22 DK DK91610058.9T patent/DK0470039T3/da active
- 1991-07-24 ZA ZA915805A patent/ZA915805B/xx unknown
- 1991-07-27 KR KR1019910012971A patent/KR100233955B1/ko not_active IP Right Cessation
- 1991-07-29 JP JP18892391A patent/JP3165181B2/ja not_active Expired - Fee Related
- 1991-07-29 FI FI913613A patent/FI99111C/fi active
- 1991-07-29 CA CA002048027A patent/CA2048027C/en not_active Expired - Fee Related
- 1991-07-29 AU AU81411/91A patent/AU646679B2/en not_active Ceased
- 1991-07-29 PT PT98483A patent/PT98483B/pt not_active IP Right Cessation
-
1993
- 1993-10-04 US US08/131,438 patent/US5393761A/en not_active Expired - Fee Related
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1995
- 1995-02-07 SG SG19995A patent/SG19995G/en unknown
- 1995-03-03 GR GR940404079T patent/GR3015274T3/el unknown
- 1995-04-06 HK HK51495A patent/HK51495A/xx not_active IP Right Cessation
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