ZA200408059B - 1- or 3-Thia benzonaphthoazulenes as inhibitors oftumour necrosis factor production and intermediat es for the preparation thereof. - Google Patents
1- or 3-Thia benzonaphthoazulenes as inhibitors oftumour necrosis factor production and intermediat es for the preparation thereof. Download PDFInfo
- Publication number
- ZA200408059B ZA200408059B ZA200408059A ZA200408059A ZA200408059B ZA 200408059 B ZA200408059 B ZA 200408059B ZA 200408059 A ZA200408059 A ZA 200408059A ZA 200408059 A ZA200408059 A ZA 200408059A ZA 200408059 B ZA200408059 B ZA 200408059B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- benzo
- thia
- oxa
- amino
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 239000003112 inhibitor Substances 0.000 title claims description 10
- QJCMSTPFSQAMGS-UHFFFAOYSA-N 16-thiapentacyclo[12.8.0.02,11.03,8.015,19]docosa-1(22),2(11),3,5,7,9,12,14,18,20-decaene Chemical class C1=CC2=CCSC2=C2C=CC3=CC=C(C=CC=C4)C4=C3C2=C1 QJCMSTPFSQAMGS-UHFFFAOYSA-N 0.000 title 1
- 230000017074 necrotic cell death Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 13
- UDEQOVGVLPGNGN-UHFFFAOYSA-N C12=CC=CC2=CC=CC2=C1C=CC1=CC=C(C=CC=C3)C3=C21 Chemical class C12=CC=CC2=CC=CC2=C1C=CC1=CC=C(C=CC=C3)C3=C21 UDEQOVGVLPGNGN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 6
- 239000000543 intermediate Substances 0.000 claims abstract description 6
- 239000012453 solvate Substances 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 130
- 150000001875 compounds Chemical class 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 34
- -1 C- C Chemical group 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000006193 alkinyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000001589 carboacyl group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 150000003573 thiols Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
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- 125000003435 aroyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 230000001575 pathological effect Effects 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 6
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- 150000001412 amines Chemical class 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
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- DCHMKTQTSPDSOR-UHFFFAOYSA-N 17-oxa-5-thiapentacyclo[12.8.0.02,6.07,12.016,21]docosa-1(22),2(6),3,7,9,11,13,15,18,20-decaen-4-ylmethanol Chemical compound S1C(=CC=2C=3C(=CC4=C(C1=2)C=CC=C4)C=C1OC=CC=C1C=3)CO DCHMKTQTSPDSOR-UHFFFAOYSA-N 0.000 claims 1
- DVIYFORSMOIXAU-UHFFFAOYSA-N 3-(3,13-dithiapentacyclo[12.8.0.02,6.07,12.015,20]docosa-1(14),2(6),4,7,9,11,15,17,19,21-decaen-4-ylmethoxy)-N,N-dimethylpropan-1-amine Chemical compound C12=CC=C3C=CC=CC3=C2SC2=CC=CC=C2C2=C1SC(COCCCN(C)C)=C2 DVIYFORSMOIXAU-UHFFFAOYSA-N 0.000 claims 1
- LXRQZMPICWJCMQ-UHFFFAOYSA-N 3-(5,17-dithiapentacyclo[12.8.0.02,6.07,12.016,21]docosa-1(22),2(6),3,7,9,11,13,15,18,20-decaen-4-ylmethoxy)-N,N-dimethylpropan-1-amine Chemical compound CN(CCCOCC1=CC=2C=3C(=CC4=C(C=2S1)C=CC=C4)C=C1SC=CC=C1C=3)C LXRQZMPICWJCMQ-UHFFFAOYSA-N 0.000 claims 1
- UPZTVZXRDRCIDJ-UHFFFAOYSA-N 3-[(11-methoxy-17-oxa-5-thiapentacyclo[12.8.0.02,6.07,12.016,21]docosa-1(22),2(6),3,7(12),8,10,13,15,18,20-decaen-4-yl)methoxy]-N,N-dimethylpropan-1-amine Chemical compound CN(CCCOCC1=CC=2C=3C(=CC4=C(C=2S1)C=CC=C4OC)C=C1OC=CC=C1C=3)C UPZTVZXRDRCIDJ-UHFFFAOYSA-N 0.000 claims 1
- CMMVDEBZLXCIRQ-UHFFFAOYSA-N 5,17-dithiapentacyclo[12.8.0.02,6.07,12.016,21]docosa-1(22),2(6),3,7,9,11,13,15,18,20-decaen-4-ylmethanol Chemical compound S1C(=CC=2C=3C(=CC4=C(C1=2)C=CC=C4)C=C1SC=CC=C1C=3)CO CMMVDEBZLXCIRQ-UHFFFAOYSA-N 0.000 claims 1
- PPSCUNMOKPTDCY-UHFFFAOYSA-N C12=CC=C3C=CC=CC3=C2OC2=CC=CC=C2C2=C1SC(C(=O)OCC)=C2 Chemical compound C12=CC=C3C=CC=CC3=C2OC2=CC=CC=C2C2=C1SC(C(=O)OCC)=C2 PPSCUNMOKPTDCY-UHFFFAOYSA-N 0.000 claims 1
- VSEQQHIQUDAUCA-UHFFFAOYSA-N C12=CC=C3C=CC=CC3=C2SC2=CC=CC=C2C2=C1SC(C(=O)OCC)=C2 Chemical compound C12=CC=C3C=CC=CC3=C2SC2=CC=CC=C2C2=C1SC(C(=O)OCC)=C2 VSEQQHIQUDAUCA-UHFFFAOYSA-N 0.000 claims 1
- DBABROWULCRABO-UHFFFAOYSA-N C12=CC=C3C=CC=CC3=C2SC2=CC=CC=C2C2=C1SC(COCCN(C)C)=C2 Chemical compound C12=CC=C3C=CC=CC3=C2SC2=CC=CC=C2C2=C1SC(COCCN(C)C)=C2 DBABROWULCRABO-UHFFFAOYSA-N 0.000 claims 1
- TXHZGALBBHHMCB-UHFFFAOYSA-N C12=CC=C3CCCCC3=C2OC2=CC=CC=C2C2=C1SC(CO)=C2 Chemical compound C12=CC=C3CCCCC3=C2OC2=CC=CC=C2C2=C1SC(CO)=C2 TXHZGALBBHHMCB-UHFFFAOYSA-N 0.000 claims 1
- AJORSXHYHIQEFE-UHFFFAOYSA-N C12=CC=C3CCCCC3=C2OC2=CC=CC=C2C2=C1SC(COCCCN)=C2 Chemical compound C12=CC=C3CCCCC3=C2OC2=CC=CC=C2C2=C1SC(COCCCN)=C2 AJORSXHYHIQEFE-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HR20020303A HRP20020303A8 (en) | 2002-04-10 | 2002-04-10 | Benzonaphthoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
Publications (1)
Publication Number | Publication Date |
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ZA200408059B true ZA200408059B (en) | 2005-10-06 |
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Family Applications (1)
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ZA200408059A ZA200408059B (en) | 2002-04-10 | 2004-10-06 | 1- or 3-Thia benzonaphthoazulenes as inhibitors oftumour necrosis factor production and intermediat es for the preparation thereof. |
Country Status (24)
Country | Link |
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US (2) | US20050137249A1 (ko) |
EP (1) | EP1492795B1 (ko) |
JP (1) | JP2005526827A (ko) |
KR (1) | KR20050014806A (ko) |
CN (1) | CN1649876A (ko) |
AT (1) | ATE310005T1 (ko) |
AU (1) | AU2003259958A1 (ko) |
BR (1) | BR0309097A (ko) |
CA (1) | CA2481850A1 (ko) |
DE (1) | DE60302344T2 (ko) |
ES (1) | ES2253694T3 (ko) |
HR (1) | HRP20020303A8 (ko) |
IL (1) | IL164395A0 (ko) |
IS (1) | IS7472A (ko) |
MX (1) | MXPA04009872A (ko) |
NO (1) | NO20044508L (ko) |
NZ (1) | NZ535622A (ko) |
PL (1) | PL374005A1 (ko) |
RU (1) | RU2318827C2 (ko) |
SI (1) | SI1492795T1 (ko) |
UA (1) | UA78297C2 (ko) |
WO (1) | WO2003084961A1 (ko) |
YU (1) | YU88104A (ko) |
ZA (1) | ZA200408059B (ko) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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HRP20020304B1 (en) * | 2002-04-10 | 2008-04-30 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | 1-oxa-3-aza-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the production thereof |
HRP20030160A2 (en) * | 2003-03-06 | 2005-04-30 | Pliva-Istra�iva�ki institut d.o.o. | 1-thiadibenzoazulene derivatives and biological action thereof |
HRP20030955A2 (en) * | 2003-11-21 | 2005-08-31 | Pliva-Istra�iva�ki institut d.o.o. | USE OF 1-OXADIBENZO[e,h]AZULENES FOR THE MANUFACTURE OF PHARMACEUTICAL FORMULATIONS FOR THE TREATMENT AND PREVENTION OF CENTRAL NERVOUS SYSTEM DISEASES AND DISORDERS |
HRP20030954A2 (en) * | 2003-11-21 | 2005-08-31 | Pliva D.D. | USE OF 1-AZA-DIBENZO[e,h]AZULENES FOR THE MANUFACTURENT AND PREVENTION OF CENTRAL NERVOUS SYSTEM DISEASES AND DISORDERS |
HRP20040104A2 (en) * | 2004-01-30 | 2005-10-31 | Pliva-Istra�iva�ki institut d.o.o. | Use of benzonaphthoazulenes for the manufacture of pharmaceutical formulations for the treatment and prevention of central nervous system diseases and disorders |
KR20120037913A (ko) * | 2009-07-28 | 2012-04-20 | 니폰 조키 세야쿠 가부시키가이샤 | 티아벤조아줄렌프로피온산 유도체의 제조법 |
CA2837858C (en) * | 2011-06-02 | 2022-05-03 | The Regents Of The University Of California | Blockade of inflammatory proteases with theta - defensins |
CN104163811A (zh) * | 2013-05-16 | 2014-11-26 | 重庆圣华曦药业股份有限公司 | 一种制备度洛西汀盐酸盐的新方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US3711489A (en) * | 1971-03-31 | 1973-01-16 | Pfizer | Certain 8,9-dihydro(3,4,7,8)cycloocta(1,2-d)imidazoles |
CA967573A (en) | 1972-12-22 | 1975-05-13 | Joseph G. Lombardino | Tetracyclic anti-inflammatory agents |
US4198421A (en) * | 1978-11-30 | 1980-04-15 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2-substituted-dibenzo[2,3:6,7]oxepino[4,5-d]imidazoles |
HRP20000310A2 (en) | 2000-05-17 | 2002-02-28 | Pliva Farmaceutska Ind Dioniko | New dibenzoazulene compounds as tumor necrosis factor inhibitors |
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2002
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2003
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- 2003-04-09 US US10/510,867 patent/US20050137249A1/en not_active Abandoned
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2004
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Also Published As
Publication number | Publication date |
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US20050130964A1 (en) | 2005-06-16 |
EP1492795B1 (en) | 2005-11-16 |
KR20050014806A (ko) | 2005-02-07 |
AU2003259958A1 (en) | 2003-10-20 |
CA2481850A1 (en) | 2003-10-16 |
US7262309B2 (en) | 2007-08-28 |
PL374005A1 (en) | 2005-09-19 |
DE60302344T2 (de) | 2006-07-27 |
US20050137249A1 (en) | 2005-06-23 |
HRP20020303B8 (en) | 2009-03-31 |
NZ535622A (en) | 2006-03-31 |
HRP20020303A2 (en) | 2003-10-31 |
ATE310005T1 (de) | 2005-12-15 |
BR0309097A (pt) | 2005-02-09 |
WO2003084961A1 (en) | 2003-10-16 |
ES2253694T3 (es) | 2006-06-01 |
RU2318827C2 (ru) | 2008-03-10 |
JP2005526827A (ja) | 2005-09-08 |
NO20044508L (no) | 2004-11-09 |
RU2004132866A (ru) | 2005-06-10 |
HRP20020303A8 (en) | 2009-03-31 |
UA78297C2 (en) | 2007-03-15 |
DE60302344D1 (de) | 2005-12-22 |
IS7472A (is) | 2004-09-27 |
SI1492795T1 (sl) | 2006-04-30 |
EP1492795A1 (en) | 2005-01-05 |
HRP20020303B1 (en) | 2007-05-31 |
MXPA04009872A (es) | 2005-08-16 |
YU88104A (sh) | 2006-08-17 |
IL164395A0 (en) | 2005-12-18 |
CN1649876A (zh) | 2005-08-03 |
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