DE2526354A1 - Neue spiroheterocyclanische verbindungen, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen - Google Patents
Neue spiroheterocyclanische verbindungen, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungenInfo
- Publication number
- DE2526354A1 DE2526354A1 DE19752526354 DE2526354A DE2526354A1 DE 2526354 A1 DE2526354 A1 DE 2526354A1 DE 19752526354 DE19752526354 DE 19752526354 DE 2526354 A DE2526354 A DE 2526354A DE 2526354 A1 DE2526354 A1 DE 2526354A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- pharmaceutical compositions
- methyl
- acid
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 10
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- -1 alkyl radical Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000004054 inflammatory process Effects 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 230000001562 ulcerogenic effect Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 208000008035 Back Pain Diseases 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 206010053692 Wound complication Diseases 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- DDKMFOUTRRODRE-UHFFFAOYSA-N chloromethanone Chemical compound Cl[C]=O DDKMFOUTRRODRE-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 208000018937 joint inflammation Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7420346A FR2274292A1 (fr) | 1974-06-12 | 1974-06-12 | Nouveaux composes spiroheterocyclaniques, leur procede de preparation et leur application comme medicament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2526354A1 true DE2526354A1 (de) | 1976-01-02 |
Family
ID=9139949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752526354 Pending DE2526354A1 (de) | 1974-06-12 | 1975-06-12 | Neue spiroheterocyclanische verbindungen, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS518273A (enExample) |
| AU (1) | AU8198575A (enExample) |
| BE (1) | BE830114A (enExample) |
| DD (1) | DD118280A5 (enExample) |
| DE (1) | DE2526354A1 (enExample) |
| DK (1) | DK265175A (enExample) |
| ES (1) | ES438446A1 (enExample) |
| FR (1) | FR2274292A1 (enExample) |
| GB (1) | GB1457222A (enExample) |
| IE (1) | IE41294B1 (enExample) |
| IL (1) | IL47396A0 (enExample) |
| LU (1) | LU72712A1 (enExample) |
| NL (1) | NL7507040A (enExample) |
| SE (1) | SE7505966L (enExample) |
| ZA (1) | ZA753783B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL179957C (nl) * | 1980-03-21 | 1986-12-01 | Philips Nv | Halogeengloeilamp. |
-
1974
- 1974-06-12 FR FR7420346A patent/FR2274292A1/fr active Granted
-
1975
- 1975-05-26 SE SE7505966A patent/SE7505966L/xx unknown
- 1975-05-30 IL IL47396A patent/IL47396A0/xx unknown
- 1975-06-09 JP JP50068674A patent/JPS518273A/ja active Pending
- 1975-06-10 AU AU81985/75A patent/AU8198575A/en not_active Expired
- 1975-06-10 DD DD186553A patent/DD118280A5/xx unknown
- 1975-06-11 BE BE157229A patent/BE830114A/xx unknown
- 1975-06-11 ES ES438446A patent/ES438446A1/es not_active Expired
- 1975-06-11 GB GB2504475A patent/GB1457222A/en not_active Expired
- 1975-06-11 LU LU72712A patent/LU72712A1/xx unknown
- 1975-06-12 NL NL7507040A patent/NL7507040A/xx unknown
- 1975-06-12 IE IE1325/75A patent/IE41294B1/xx unknown
- 1975-06-12 ZA ZA00753783A patent/ZA753783B/xx unknown
- 1975-06-12 DE DE19752526354 patent/DE2526354A1/de active Pending
- 1975-06-12 DK DK265175A patent/DK265175A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS518273A (enExample) | 1976-01-23 |
| ZA753783B (en) | 1976-06-30 |
| IL47396A0 (en) | 1975-07-28 |
| NL7507040A (nl) | 1975-12-16 |
| DK265175A (da) | 1975-12-13 |
| LU72712A1 (enExample) | 1976-04-13 |
| IE41294B1 (en) | 1979-12-05 |
| GB1457222A (en) | 1976-12-01 |
| DD118280A5 (enExample) | 1976-02-20 |
| AU8198575A (en) | 1976-12-16 |
| FR2274292A1 (fr) | 1976-01-09 |
| FR2274292B1 (enExample) | 1978-06-30 |
| SE7505966L (sv) | 1975-12-15 |
| IE41294L (en) | 1975-12-12 |
| BE830114A (fr) | 1975-12-11 |
| ES438446A1 (es) | 1977-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |