AU686210B2 - Eosinophil chemotaxis inhibitor - Google Patents
Eosinophil chemotaxis inhibitor Download PDFInfo
- Publication number
- AU686210B2 AU686210B2 AU72926/94A AU7292694A AU686210B2 AU 686210 B2 AU686210 B2 AU 686210B2 AU 72926/94 A AU72926/94 A AU 72926/94A AU 7292694 A AU7292694 A AU 7292694A AU 686210 B2 AU686210 B2 AU 686210B2
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- AU
- Australia
- Prior art keywords
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- hydrogen atom
- atom
- alkyl group
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000013764 eosinophil chemotaxis Effects 0.000 title description 8
- 229940105129 Chemotaxis inhibitor Drugs 0.000 title description 3
- 239000002819 chemotaxis inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- -1 amino, carboxyl Chemical group 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 201000008937 atopic dermatitis Diseases 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 9
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
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- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 208000010753 nasal discharge Diseases 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical group [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- KAAKNAVDUBSDJF-UHFFFAOYSA-N palladium;trimethylphosphane Chemical compound [Pd].CP(C)C.CP(C)C KAAKNAVDUBSDJF-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 108060007951 sulfatase Proteins 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 231100000721 toxic potential Toxicity 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5-234764 | 1993-09-21 | ||
| JP23476493 | 1993-09-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7292694A AU7292694A (en) | 1995-04-06 |
| AU686210B2 true AU686210B2 (en) | 1998-02-05 |
Family
ID=16975996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU72926/94A Ceased AU686210B2 (en) | 1993-09-21 | 1994-09-12 | Eosinophil chemotaxis inhibitor |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US5922712A (https=) |
| EP (2) | EP0865790A3 (https=) |
| KR (1) | KR100280240B1 (https=) |
| CN (1) | CN1109885A (https=) |
| AU (1) | AU686210B2 (https=) |
| CA (1) | CA2132489A1 (https=) |
| FI (1) | FI944354A0 (https=) |
| NO (1) | NO307547B1 (https=) |
| NZ (1) | NZ264479A (https=) |
| TW (1) | TW304878B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2156252C2 (ru) * | 1994-09-16 | 2000-09-20 | Такеда Кемикал Индастриз, Лтд. | Триазолопиридазины, способ их получения, фармацевтические композиции на их основе и способ лечения |
| CA2285264A1 (en) | 1997-04-25 | 1998-11-05 | Michiyo Gyoten | Condensed pyridazine derivatives, their production and use |
| WO1999044611A1 (en) * | 1998-03-04 | 1999-09-10 | Takeda Chemical Industries, Ltd. | Triazolo-pyridazine derivatives for the treatment of chronic obstructive pulmonary diseases |
| CA2346659A1 (en) | 1998-10-06 | 2000-04-13 | Michiyo Gyoten | Condensed pyridazine compounds, their production and use |
| KR20010087738A (ko) | 1998-10-21 | 2001-09-21 | 다케다 야쿠힌 고교 가부시키가이샤 | 축합 피리다진 유도체, 이의 제조 방법 및 용도 |
| AU7315900A (en) * | 1999-09-20 | 2001-04-24 | Takeda Chemical Industries Ltd. | Chemokine/cytokine expression inhibitors |
| CA2390919A1 (en) * | 1999-11-11 | 2001-05-17 | Takeda Chemical Industries, Ltd. | Nose drop containing condensed pyridazine |
| HUE030390T2 (en) | 2005-12-21 | 2017-05-29 | Janssen Pharmaceutica Nv | Triazolopyridazines as tyrosine kinase modulators |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0185346A2 (de) * | 1984-12-21 | 1986-06-25 | Dr. Karl Thomae GmbH | Neue Imidazoderivate, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel |
| EP0440119A1 (en) * | 1990-01-31 | 1991-08-07 | Takeda Chemical Industries, Ltd. | Imidazopyridazine compounds, their production and use |
| EP0445549A1 (de) * | 1990-03-08 | 1991-09-11 | Precitronic Gesellschaft für Feinmechanik und Electronic m.b.H | Pyrotechnische Vorrichtung |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8826205D0 (en) * | 1988-11-09 | 1988-12-14 | Wellcome Found | Heterocyclic compounds |
| PH27291A (en) * | 1989-01-31 | 1993-05-04 | Takeda Chemical Industries Ltd | Imidazolpyrimidazines their production and use |
| US5011835A (en) * | 1990-02-07 | 1991-04-30 | Merrell Dow Pharmaceuticals Inc. | Substituted triazolopyridazines, pharmaceutical compositions and use |
| DE69106902T2 (de) * | 1990-03-01 | 1995-07-06 | Takeda Chemical Industries Ltd | Imidazopyridazine, ihre Herstellung und Verwendung. |
| CA2097317C (en) * | 1990-12-14 | 2002-02-12 | Albert A. Carr | Antiallergic piperdinyl benzimidazoles |
| TW211013B (https=) * | 1991-12-27 | 1993-08-11 | Takeda Pharm Industry Co Ltd | |
| LT3200B (en) * | 1992-03-18 | 1995-03-27 | Takeda Chemical Industries Ltd | Triazolopyridazine methodfor production thereof and use |
| EP0562440B1 (en) * | 1992-03-18 | 1998-12-23 | Takeda Chemical Industries, Ltd. | Imidazopyridazines as antiasthmatics |
-
1994
- 1994-09-09 TW TW083108317A patent/TW304878B/zh active
- 1994-09-12 AU AU72926/94A patent/AU686210B2/en not_active Ceased
- 1994-09-17 EP EP98110050A patent/EP0865790A3/en not_active Withdrawn
- 1994-09-17 KR KR1019940023814A patent/KR100280240B1/ko not_active Expired - Fee Related
- 1994-09-17 EP EP94114661A patent/EP0648491A3/en not_active Withdrawn
- 1994-09-19 NZ NZ264479A patent/NZ264479A/xx unknown
- 1994-09-20 NO NO943494A patent/NO307547B1/no not_active IP Right Cessation
- 1994-09-20 CA CA002132489A patent/CA2132489A1/en not_active Abandoned
- 1994-09-20 FI FI944354A patent/FI944354A0/fi unknown
- 1994-09-20 CN CN94115326A patent/CN1109885A/zh active Pending
-
1998
- 1998-05-01 US US09/070,928 patent/US5922712A/en not_active Expired - Fee Related
-
1999
- 1999-02-16 US US09/250,392 patent/US5945419A/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0185346A2 (de) * | 1984-12-21 | 1986-06-25 | Dr. Karl Thomae GmbH | Neue Imidazoderivate, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel |
| EP0440119A1 (en) * | 1990-01-31 | 1991-08-07 | Takeda Chemical Industries, Ltd. | Imidazopyridazine compounds, their production and use |
| EP0445549A1 (de) * | 1990-03-08 | 1991-09-11 | Precitronic Gesellschaft für Feinmechanik und Electronic m.b.H | Pyrotechnische Vorrichtung |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100280240B1 (ko) | 2001-02-01 |
| US5922712A (en) | 1999-07-13 |
| FI944354A0 (fi) | 1994-09-20 |
| EP0648491A3 (en) | 1995-07-19 |
| AU7292694A (en) | 1995-04-06 |
| EP0648491A2 (en) | 1995-04-19 |
| NO307547B1 (no) | 2000-04-25 |
| CA2132489A1 (en) | 1995-03-22 |
| US5945419A (en) | 1999-08-31 |
| EP0865790A2 (en) | 1998-09-23 |
| CN1109885A (zh) | 1995-10-11 |
| NZ264479A (en) | 1999-05-28 |
| TW304878B (https=) | 1997-05-11 |
| NO943494D0 (no) | 1994-09-20 |
| NO943494L (no) | 1995-03-22 |
| EP0865790A3 (en) | 1999-03-10 |
| KR950007851A (ko) | 1995-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |