FI113643B - Aryloxicykloalkenyl- och aryloxiiminocykloalkenylhydroxiureor som 5-lipoxygenasinhibitorer - Google Patents
Aryloxicykloalkenyl- och aryloxiiminocykloalkenylhydroxiureor som 5-lipoxygenasinhibitorer Download PDFInfo
- Publication number
- FI113643B FI113643B FI971994A FI971994A FI113643B FI 113643 B FI113643 B FI 113643B FI 971994 A FI971994 A FI 971994A FI 971994 A FI971994 A FI 971994A FI 113643 B FI113643 B FI 113643B
- Authority
- FI
- Finland
- Prior art keywords
- cyclopenten
- fluorophenoxy
- hydroxyurea
- trans
- mmol
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- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003710 calcium ionophore Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- GFMLEKMTZRGYMQ-UHFFFAOYSA-N carboxy(hydroxy)carbamic acid Chemical compound OC(=O)N(O)C(O)=O GFMLEKMTZRGYMQ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical group 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- MBVZEDIBUZMQOR-UHFFFAOYSA-N cyclopenten-1-yl acetate Chemical compound CC(=O)OC1=CCCC1 MBVZEDIBUZMQOR-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- CJAONIOAQZUHPN-KKLWWLSJSA-N ethyl 12-[[2-[(2r,3r)-3-[2-[(12-ethoxy-12-oxododecyl)-methylamino]-2-oxoethoxy]butan-2-yl]oxyacetyl]-methylamino]dodecanoate Chemical compound CCOC(=O)CCCCCCCCCCCN(C)C(=O)CO[C@H](C)[C@@H](C)OCC(=O)N(C)CCCCCCCCCCCC(=O)OCC CJAONIOAQZUHPN-KKLWWLSJSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000002977 hyperthermial effect Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- DBTXKJJSFWZJNS-UHFFFAOYSA-N o-phenylhydroxylamine;hydrochloride Chemical compound Cl.NOC1=CC=CC=C1 DBTXKJJSFWZJNS-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- AGOSGCWATIJZHQ-UHFFFAOYSA-N tert-butyl [(2-methylpropan-2-yl)oxycarbonylamino] carbonate Chemical compound CC(C)(C)OC(=O)NOC(=O)OC(C)(C)C AGOSGCWATIJZHQ-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- 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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (8)
1. Förening, kännetecknad därav, att den har formeln
5 OM mhz ivr γ y υ 10 där Ar är vald ur gruppen (a) fenyl och bifenyl, som kan vara substituerade med en substituent, som är vald ur gruppen halogen, cyan, fenyl, som kan vara substituerad 15 med halogen, och fenoxi, som kan vara substituerad med halogen; X är vald ur gruppen -Q1- och -(CHR1)-0-N=, varvid N= -gruppen är bunden tili cykloalkenringen; och varvid Q1 är O eller CH=N-0; och R1 är väte; pär 1; Y är väte eller C^-alkyl;
20 Z är väte; och M är väte eller en farmaceutiskt godtagbar katjon.
2. Förening enligt patentkrav 1, kännetecknad därav, attAr :T: är vald ur gruppen (a), Y och Z är vardera väteatomer, p är 1 och M är väte el- ler en farmaceutiskt godtagbar katjon. 25 3. Förening enligt patentkrav 2, kännetecknad därav, attAr är fenyl, fluorfenyl, cyanfenyl, bifenyl eller fluorfenoxifenyl och X är O, som är bunden tili 4-ställningen i cykloalkenringen. • · · * 4. Förening enligt patentkrav 2, kännetecknad därav, att Ar är fenyl eller fluorfenyl och X är CH=N-0, som är bunden tili 4-ställningen i cyk-·;;; 30 loalkenringen.
5. Förening enligt patentkrav 2, kännetecknad därav, att Ar : ’ * j är fenyl eller fluorfenyl och X är CH2-0-N=, som är bunden tili 4-ställningen i I I , cykloalkenringen. *’ 6. Förening enligt patentkrav 1, kännetecknad därav, att > 35 den är vald ur gruppen 113643 25 N-{(1R,4R)-trans-4-(4-fluorfenoxi)-2-cyklopenten-1-yl}-N- hydroxiurea; N-{(1R,4R)-trans-4-[3-(4-fluorfenoxi)fenoxi]-2-cyklopenten-1-yl}-N- hydroxiurea;
5 N-{(1S,4R)-cis-4-[3-(4-fluorfenoxi)fenoxi]-2-cyklopenten-1-yl}-N- hydroxiurea; N-{(1R)-4-bensyloxiimino-2-cyklopenten-1-yl}-N-hydroxiurea; och N-{(1R)-4-(4-fluorbensyloxiimino)-2-cyklopenten-1-yl}-N- hydroxiurea;
7. Farmaceutisk komposition, som är avsedd för behandling av ett sadant medicinskt tillstand hos ett däggdjur, som kräver en 5-lipoxygenasinhibitor, kännetecknad därav, att den innehäller en tera-peutiskt effektiv mängd av en förening enligt patentkrav 1 och en farmaceutiskt godtagbar bärare eller ett utspädningsmedel.
8. Farmaceutisk komposition enlig patentkrav 7, känne tecknad därav, att det medicinska tillständet är en inflammationssjukdom, allergi eller en kardiovaskulär sjukdom. * · · * · · » • » · « < » • « » • * · • · · • · • · • * · • f · • · · » » * » • · • · • · # • * • · ' • · * · t I I • »
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9401897 | 1994-11-10 | ||
| JP9401897 | 1994-11-10 | ||
| IB9500399 | 1995-05-26 | ||
| PCT/IB1995/000399 WO1996015106A1 (en) | 1994-11-10 | 1995-05-26 | Aryloxycycloalkenyl and aryloxyiminocycloalkenylhydroxyureas as 5-lipoxygenase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI971994A FI971994A (sv) | 1997-05-09 |
| FI971994A0 FI971994A0 (sv) | 1997-05-09 |
| FI113643B true FI113643B (sv) | 2004-05-31 |
Family
ID=14098792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI971994A FI113643B (sv) | 1994-11-10 | 1997-05-09 | Aryloxicykloalkenyl- och aryloxiiminocykloalkenylhydroxiureor som 5-lipoxygenasinhibitorer |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5798383A (sv) |
| EP (1) | EP0790981B1 (sv) |
| KR (1) | KR0182321B1 (sv) |
| AR (1) | AR002239A1 (sv) |
| AT (1) | ATE184272T1 (sv) |
| AU (1) | AU690354B2 (sv) |
| BR (1) | BR9505130A (sv) |
| CA (1) | CA2205033C (sv) |
| CO (1) | CO4520227A1 (sv) |
| CZ (1) | CZ282832B6 (sv) |
| DE (1) | DE69512080T2 (sv) |
| ES (1) | ES2135066T3 (sv) |
| FI (1) | FI113643B (sv) |
| GR (1) | GR3031378T3 (sv) |
| IL (1) | IL115853A (sv) |
| MX (1) | MX9703485A (sv) |
| MY (1) | MY112595A (sv) |
| NO (1) | NO305362B1 (sv) |
| NZ (1) | NZ280434A (sv) |
| PE (1) | PE49596A1 (sv) |
| PL (1) | PL179023B1 (sv) |
| RU (1) | RU2119479C1 (sv) |
| SG (1) | SG44332A1 (sv) |
| TR (1) | TR199501413A2 (sv) |
| TW (1) | TW363960B (sv) |
| WO (1) | WO1996015106A1 (sv) |
| ZA (1) | ZA959512B (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0217294D0 (en) * | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicaments |
| KR102557875B1 (ko) * | 2017-02-03 | 2023-07-20 | 닛산 가가쿠 가부시키가이샤 | 우레아결합을 갖는 구조단위를 갖는 폴리머를 포함하는 레지스트 하층막 형성 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3007138B2 (ja) * | 1990-11-27 | 2000-02-07 | ファイザー製薬株式会社 | 新規なヒドロキサム酸とｎ―ヒドロキシ尿素誘導体およびそれらの組成物 |
| US5326883A (en) * | 1992-12-18 | 1994-07-05 | Abbott Laboratories | Oxime ether derivatives having lipoxygenase inhibitory activity |
| EP0693054B1 (en) * | 1993-04-07 | 1998-06-10 | Pfizer Inc. | Cycloalkylhydroxyureas and their use as lipoxygenase inhibitors |
| TW418089B (en) * | 1993-08-19 | 2001-01-11 | Pfizer | Pharmaceutical composition comprising phenoxyphenyl cyclopentenyl hydroxyureas (the dextrorotary isomers) |
-
1995
- 1995-05-26 CA CA002205033A patent/CA2205033C/en not_active Expired - Fee Related
- 1995-05-26 WO PCT/IB1995/000399 patent/WO1996015106A1/en active IP Right Grant
- 1995-05-26 MX MX9703485A patent/MX9703485A/es unknown
- 1995-05-26 ES ES95918112T patent/ES2135066T3/es not_active Expired - Lifetime
- 1995-05-26 US US08/836,452 patent/US5798383A/en not_active Expired - Fee Related
- 1995-05-26 EP EP95918112A patent/EP0790981B1/en not_active Expired - Lifetime
- 1995-05-26 AT AT95918112T patent/ATE184272T1/de not_active IP Right Cessation
- 1995-05-26 DE DE69512080T patent/DE69512080T2/de not_active Expired - Fee Related
- 1995-10-30 MY MYPI95003267A patent/MY112595A/en unknown
- 1995-11-01 AR ARP950100014A patent/AR002239A1/es unknown
- 1995-11-02 IL IL11585395A patent/IL115853A/xx active IP Right Grant
- 1995-11-03 SG SG1995001721A patent/SG44332A1/en unknown
- 1995-11-07 PE PE1995284002A patent/PE49596A1/es not_active Application Discontinuation
- 1995-11-08 TW TW084111851A patent/TW363960B/zh active
- 1995-11-09 ZA ZA959512A patent/ZA959512B/xx unknown
- 1995-11-09 CZ CZ952942A patent/CZ282832B6/cs not_active IP Right Cessation
- 1995-11-09 KR KR1019950040425A patent/KR0182321B1/ko not_active IP Right Cessation
- 1995-11-09 RU RU95119414/04A patent/RU2119479C1/ru not_active IP Right Cessation
- 1995-11-09 BR BR9505130A patent/BR9505130A/pt not_active IP Right Cessation
- 1995-11-09 NO NO954530A patent/NO305362B1/no not_active IP Right Cessation
- 1995-11-09 PL PL95311325A patent/PL179023B1/pl unknown
- 1995-11-09 AU AU37764/95A patent/AU690354B2/en not_active Ceased
- 1995-11-09 NZ NZ280434A patent/NZ280434A/en unknown
- 1995-11-10 CO CO95053260A patent/CO4520227A1/es unknown
- 1995-11-10 TR TR95/01413A patent/TR199501413A2/xx unknown
-
1997
- 1997-05-09 FI FI971994A patent/FI113643B/sv not_active IP Right Cessation
-
1999
- 1999-09-29 GR GR990402472T patent/GR3031378T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |